SCIENTIFIC ABSTRACT KOCHETKOV, N.K. - KOCHETKOV, N.K.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R000723510015-7
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: September 19, 2001
• Sequence Number: 15
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

ME

XWHMT, SA.1 IMUMT* Mol ALIMA. X&Ao
b"tion of , With 0-41carbomyl compounds,
Pm 4t synthesis of vlarlops of 0 -keto &aid esters, Shw, ",
Wv4 Ag 157. (KM IOSO
10 mlio'vskly gosu&rstv*nW univereltat I lastitut farmakologil
I kMalotorapil Ak"evdl o"Itaiaskikh nauk SM.
(112W1 aoqWMS) (Aaldso Oreade)

=am -AYMOBB Flag
A ON

X.1 TIMMAWYA, T*N,
.1rathasis of Aryl -0 - ketosell of 11271snuoses Ald wyla a
ketones of vliWIlulfGjddsl6 Shvroot,khIs# 27 00,1012743-:40
0 13? 0 (Nm U14)
I,Noskavskly, gosaderst"My wAversitate
(zotems)

U-I 2 -2/43
AUT901R., KOdb*UoV# X. Xj, Xb=llno A. To.
TI=: Derivatives or (192..2 ]hop %a n9(PrdsvcdrM.bIt#Lklo(1,,2,2)
gePtsn&). In. 2-Aa7UICya*jI ~e JJ-2-huptems ond Some of Their
Reactions (2-At$Ub:it&Uao(,1,2,',2ipptoa-2 I nekotoryye ikh rvaktsil)
PUIOMCAL: Zhurnal obohdwy kh's". 1Mj, Vol 2T,, Ir 12p pp 3182 - 3189-(M=)
A&TMAM Reaction. of 5 #,, P.N*C^O=tCWL vith 5-3 9- eYdopeatedlens o"r-
night In petrolmm other gave 75% 2-(P-tolzwl)-3-chlorobicyclotl,,12,,21-
ble -5-4mP.A. 91.~ - 20 (ItOM). Slodlarly were obt&U*d.- 80% '
4
p-ohloroUmsoyl)-3-chlmoblcycloll,92,,2)bovt-5.4m(l),, 04 gh.5,- 50;
2
2-(P-nitrdboaMl)-3-cUorobloyalotl#2,92)bept-5-ene.. m. 147 - 80
71p
ME). Rydrogenation, or I over Pd gave 2-(p-chlorvbenzqyl)bjLcy*Io-
1#2#21haptem,p a. 109 - 9*5'0 (ft0g); such b7drogenations proc*ed
i
jCO than In ZtM or ZtgO. Boatixg 40 g., 2-acetyl-
3-dkIoroblcy*Iojl,q2p2)b*ptww in C6% with 100 al, ft3N and a littio
Iydroquinow 2D - 5 bra. at reflux gave a precipitate of Et X,,Wl
and a riltrato &lob yielded 50 2-amtyIbIcyclojIO2,p2j-hea-l-ew
(n),, b 62 - 6% b5 76 - 800 n2O i.4ms d2o 1.0102 (a lacriuator)p
3.4 D
Card 1/3

Derivat1ves of Bicydb (Cant)
ihoss 2ph- W --anylbydrasaw has s. 153* (abs, max. 30 a is). Similarly
a i 7T.4% 2-Pv9QVlbIcyc1,Djl,2,,2)
hept-2-ens (in), b2 59 1649500 _dj 0.9965; (2ph-d1nItrqbwwlbDdrw-
lam Vith A6 145.5 - 6*t abs. Nut 30 - rO a p ). Similarly prepared from ths
3-ddoro darivative vas 74-4 2-butyMlbicycloils,2j,2]bept-2-et*,, b3 82 - VJV
n20 1.4915p d20 0.9861 x6 129 - ~Tp abs. max.
A - 70 up), DOI-11 twestwat of 2-bftzoyl-3-chlorobit,"yelo(l,,42)twptom !Ith
ttjX and troatment of the anWI* product vith diluted H2Wh gave 5%
2-b*nzoylblcy,ololl,92,,21hopt-g-ow OT)p a. 80 - r ( X- 953.8 spi (2t2O); the
mother Uquor gum 20% of apparently a dimer of the above a. 130 - Pj,.*ieh
has no double bond, 11eaction of 11 With XOM(OOP)2 In 9 brs. at $0 - W gave
YlwI
after &q. Ulgtmnt 78.6% di-It 2-&cetyIbIcycloj2p2p21b*Pt-3- . p bo?
157 - 66% aw 1.472D (9 4-dinitropbetw1hydrazone* n. 130 - V UI rehws*d
6 Urs. w1th gave T4.1f 2-psop osqI-3~-ftsUq1sm1ncb icyclo lip 2p 21boptaw p
b3 89 - 90*pio 10143"0 . 0.9440; WI saltp a. 141.5, 2.50; methlodid*j, a.
UD 6126
143 - V. VOrwastIon of IV over M gave 2-bonxoyIbIcyelo(lI2j2jbept&wp blo
155 - 80-1 n-W 1.5540 (2*h-d1nItro;henylbydr"on*p m. 155 - 6*). Pa=:CR2
, D
Card 2/3

79-12-2A3
ronvatives or Dicyclo (coat)
and cyalopentadjew readily gavv " 2-benzcylblcy*Ull,,gp2lbapt-5-iM* b7
135 - 6*p 20 1.566oi brdrqpn&tIou over Pd gave the saturat*4 analogue, Tbare
1%
aft 7 references,, 5 or v&tch an sorutp I OerumO and I IbgLIsh*
AS=IM(W: skly WtItut formakologu i kh' terspli
(8clentirie Fwastrah institute of mmuscolov ,ad amattieravy)
WWI MY# 12p M6
AVAnASIX: tAbrary of Coagross
Card 3/3 1. Cyoloheptwwa-Derivatives
reactions
2. Cycloheptants-Chmical

AUTHORS: -ZacbmtkAx- N- L.9 Khomutoval Yee Deg Karpolskly, 79-12-9/43
ut Yee$ and thocutovo R. Me
TITLE: Investigation In the Series of the Icoxazol (1981940vanile
v ryadu Isoksasola)
IT. Synthesis of Some Mines of the Isolatol Series
(Sintes zekatmft aalnoy ryada Izoksuzola)
M IODICAL; Zhurnal Obahchey KhImil, 957, Vol. 27, Ur 12, pp. 3210-
-3214 (USSR)
ABSTRACT: In connection with that# recently obtained In physlologicaLl-
ly active substanceag to which the Isoxazol-eyele belongs#
too# the synthesis of some derivatives of the isoxasol.
series with an amino group In the side chain was carried
out by the authorso Thus the reaction of the 3-m*thyl-
-ohlorid*-isoxA*ol with diethylanizoothanol leads to
(isokstol-3-u*th.vl)-p-diothylaminoothyl-oth*r (see formula*).
ThIsiaxino ether foras together with ethyl Iodide a
qu&rt"7 malts which In also confirnei by Its structure.
Under the sane conditions also the 3-diethylaminomothylee
-isoxasol forms a quartarl salt, whereas a direct influence
of the 3-sathyleeehlori4e-isoxazol upon triethyl-anizo does
Card 113 not lead to the result expected. Furthermorst the authors

Investigation In the Series of the Isoxazol 79-12-9/43
IV. Synthesis of Some Aalnes of tb* Isoxasol Series
succeeded to 'bring the 3-nothyl-chloride-laoxazol In con-
densation with aromatic amIn*sj with the At* to use the
co:pounds obtained for the synthesis of the Isologues
(I ologov) of the known preparation OAnthorgano (antorgan),
havirethe isoxazol-eyole Instead of the benzene nucleus
(so* formulael). As the halide mothyl-loozatols substituted
are difficult to approach# a simple methoi of producing the
4-motbyl-ohloride-3-dimethyl-3#5-dinothyl-laoxasoI had to be
worked out, It succeeded to realize this now reaction by
means of the beating of the M-dfaothyl-lsoxazol with
paraformaldehyde In dry t0ra-tydrogon-chlorldo In the pro-
tones of hydrogen chloride. The yield of 3,5-dinothyl-4-
-nothyl-ablorlds-isoxasol asiounted to 20_30%. It was shown
that the synthesized U-phonyl-N-(395-dinothyl-isoxasolyl-4-
-mothyl)-N# ff-dialkyl-othylone-d1aalnes and the Iodine
ethllate of the 3-di*thyl-anino-mothyl-looxazol demonstrate
a weak physiologic activity. There are 7 references, 4 of
which are Slavic.
Card 2/3

T9ml2-9A3
Investigation in the Swdes of the Ismsol
IT, Synthesis of Sons Aminos of the Ismazol Series
ASSOCIATIONs Institute of Pharmcology and Chemotherapy of the
AesdemW of Medical Sciences,, VSSRj Moscow State University
(Institut farmakologii i kh'aJoterapii Akademil
moditsimkikh rAuk S=j Moskovskiy gosWarstvenra univarsitst),
SUEHMSDt October is 1956
AVAnAMXs Library of Corgress
1. Amines - Synthesla
card 3/3

mxxgm)ys 1,901,_IVAWIIW# loyest SHIDATJN9'1,1*
. . . . ...... ~- - uo,2s
opthemis of &"ty,-2-abloro-oroU&IlwfA8- 2*1- AS ISSR "?
241o-244 1 '57- (MM-U$3)
to **O"kir .rd"res"Ww univervitat to* Kove ZOM"*"**
pftata,wl#no &k%"Idkm A.I. Nola uowl "
(orcloalkenes)

AUTHORt ~~~.,Profosxor SOT-26-58-3-5/51
TITLSt The Sualsotides and Their Role in Life Processes (lukleotidy
I 1kh roll v shisnennykh protooseakh) To the Awarding of
the Nobel Prise to A. Todd (K priauthdonlyu Nobelevskoy
preall A. Toddu)
PERIODICALs Fr1roda# 19589 Nr 30 pp 32-,35 (USSR)
ABSTRACTs This Is a description of research methods employed and re-
sults obtainod by A, Todd In his research on the nuclootides
and their role In 11f* processes*
There Is 1 photo*
ASSOCIATIONo Moskovskiy gosudaretyannyy universitet ia*nt N.Y. Lomonosova
(Moscow State University Iment X.Y. Losonosov)
1. Hucleotides--ftafological effects 2. Scientific research
-USSR
Card 1/1

AUTHORSt Xochetkoyt )!,I## Cottikh, D.P., Karpsyskiyj X.Y&.# Xboxvtov# MoNo
..........
TITLE: The Configuration of P -Chlorovinylketones (0 konfigurstail
-khlorvinilketonov)
PIMIODICALs Kbinichoska a nauka i pronyahlonnost', Vol IIIg Ir 69
p 834 OJSSRI
ABSTRACTS It to supposed that jS -ablorovinylketones have a trans-con-
figurationt since the only product of the oxidation of the
sodium hypoohlorite of the mothyl-A-chlorovinylketone In the
trans-ohlorozorylla &*14.
There are 6 Govist references.
AS30CIATIONt Vauchno-jotledovatel'skiy institut faraskologil i khtmot*rapll
(Sclontifia Research Institute of Pharmacology and Chemical
Therapy)
SUBMITTEDs may 7s 1958
Card 1/1

50)
AUTBORSt Koohotkov# lox and 11fant'YeTt R.Tes
TITL2# On 5-Haloldpyromuoto Acid (0 5-g*lo1dp1roslIsovykb klelotakh)
PXRIODICAL# Tostaik lookovskogo universtUtatSorlys swWWxUkl# NaMNSWO
ss~vcnlldlp fltlkJLO khImil, v t95S,Xr 5,pp 119 - 122 (USSR)
ABSTRACTs In the synthesis of a natural combination with fursnayclo Is be-
came necessary to produce 5-halogeopyronacto acid and to taftsil-
gate the possibility of replacing the halogen Oon In theme scid*,.
The following results connected with those questions were ob.
tained j By oxidation of 5-halogun-furfurol by sodium by"broulde
the authors obtained an easy method for the synttieste of 5-bre.
sine- and 5 Iodine-pyronclo said* (outlet more than 50 %). it
w6# stated that under Influence of sodium wthrlate on *be other
of 5-bromins-pyre ole sold the" "salts the other of 5-motkoxy-
pyronsis **it. 9toulte of Zol* lasaraws were used. - The" are It
references, 3 of *blob a" Soviet#4 Gormax.3 Amaricaneand 2 USH61,
ISSOCIATIONitstedra organlehoskey Mail (Chair of Organic Chemistry)
S'UMTTXD# September 5# 1957
Card I /I
V , fV A VN

AVTIIORSs -Xochctkov, N. 1:. 0 nonutoyl, Yo. D.
TITLE:i InvOitt;Atione -in th., Saries of Iooxsk.-ola (13ZICdOV.~MA.!C v rjade
Izo%sazola) V, Subititution in .'-fint70
V tA-f6nilt:oXs&Z0lQ)
PERIODICALt Zhurnal Oba'lchey Kbinill MD, Vol- 20, rr 2, 35r
) - 3"'3 (um)
,
ABSYRACIlt A"he isoxazol dcrivutlvas were diacovered in tie ye,-ir ',!jTer.
thi3lem- tll.,; compounds of thia clasi are nalatlycly 11t.la %nown.
rt is will knoan that the Individual rqp"stht.~tjya3 ,," his clatis
of co:apounds possess the capability of nitmtin,; ("_f4:r'tCQ 1),
haloconating (reference 2)9 and alulfonatint; 3). 3ut %he
,0JItiOn of isoxazol In tho series of other am,.itlc cLii;ounja has
!jI ft-rtG not b4on determined. The 3ativitY of the iacx..-'.o1 nucleus
In the Oubstitutlon reaction ij, In con;arlocr. -.410% ot.",,2r ;,.rrLLatic
not Irvastl,:utad,. The authors Inventi-iited %!~,h' ac-1vitty of
the IsOxa2ol nualcul in the reactionu ot the 4ubuti-
tlition# such an nitration, halo,,.anablon -and n,~raLrlt"t_fois Pnej
v"ntad to determine the activity of the Ijo;.-azol nliclovz' for ex-
a.iple In comparison to the benzene nucloua. As A04.ril. c -~ - jj-1e tjj9;r
juleattd the little known 4X -phonyliaoxazol. -Itr,,, jar
of
C
d 113 cc -1Jh9n,7liG*XAZ0l with a mlzture of ailfurle J"nj M tA-C. '41-'oua acid

7;~7- 2- 1 "'11) "
jnvcvt1,;,,tIon3 In the Jerles of 19oxazola. V. Subatitu%Ivri 1r.
Zol
vuj ~vrforacd urder cooling. At A tot3l Jielsl 0; 75 7ilAtura
o~ nitro products was ellitnated, which containod 45 cj: ix
-nllrvp'~anyl looza ol rnd 50 A 01 -1-liany1nitreijoiazol. 4
-1~ikropbcnyl~--iaoxaxol in identictl vith the nv"43tanco o'jl',,~incd
fru-i j)-nitrophanyl- a -chlorovinylke tons and tho hWdrc!:'.1or!Ja of
-',.,droz,yla,jin& (ref4ronce 4), Benzolc acid vaj ql1ninated In, thQ
Oxidation of Ot -phunylnl trot soxazol with rotaajiun
Dt~aide then* two products the mixture cQntgineJ a awll :,-aoiant
(15 ',u' of the entire reaction j,roducts) of a ton-1dontifl~,J jubjImu
~4,ich probabli reprcocnts & mixture Of pol,~nltro J&,r1v4L1y4v arLi
J.titnictlcn producto. Ot -;1',hcnylbro-ao1oox4:ol vit'~ a .,,1,U of
7C 6tas obtuined by broatnation vith an lrxn catalyat b#atind#
Itj oxidation with potasaium parman(;anate ;igldg benzoic acid with
a yitld of 74 $# which contradicts a pajible preae-3co o&" a jmec(.,rA
iac..iar. The -icrcurizatlon with nercury acetate proceadi acofter
tli.an that of benzene (refe rence 5) and ilelds th4e nerc;n7 acat--tta
of oL-phenyliaoxanol vit', a 90 A 11old. In thIs connection only
the lioxazol nucleus 13 uarcurized. Z%4 poottion of t%. aubititu-
ents In the isoxazol nucleus of OC-jhQn7li3OX&ZO1 12 r.', ;Tevtnt
datun.iined In the obtained coupounds. 'A-n#j aaauni-tion V~at the.7 oc-
c,..-,.l the P-positIon 0OCn3 to Itz vell-foundod. Conclujicnzl In the
Card 2/3 :7jactions of bromInation and riarcurizatlon of 4X-pht-n;,11jOX42ol

C/64
Investigationa In the Series of Toozazols. 1. Substitution In X -nenyllsoxa-
zol
the substitution onli takes pbo* In the nucleus. In nitration It
taken j14o* as voll In the phor4l- as In the iao=zol-nucl*us# 2)
In the substitution reactions of OL -phenillaoxazol the Isoxasol
nucleus to more active than the rhonyl nucler-as Aare ars 7 re-
ferences# I 9Z wbioh is Slavic.
ASJOCIATIONt Mosacm &AU Wvorslty
(11onkovsLiy gosudarstvennyy univ*raitat)
SMUIT'I'M January 25# 1957
AVAILABLEs Library of Conjress
Card 3/3

soy / 19-2S-6-15163
AUTHORS t goohetkovo- I.-LI 4*ttikh7 B. Pot Kud"Ashovq Ls L
..............
TITL11 The Conversion of $-Chlorovinylkotones With P-Dioarbosyl
Compounds (11sim-,doystviyo P-Mlorylailketonoy a P-41kar-
bonillayal 667 din*niya&i) V. totovinylation of 4-Alk;yl Ace-
toacetto later: (V, lotovinillrovaniye a-alkilatootoukaus-
zykh efirov)
MIODICALs Zhurnal obabohey khlalij 1958, Vol. 28, Ir 69 ppe 1508-1511
(USSR)
ABSTRACT: In continuation of the previous papers on the syntbisis of
1-ketoalk*nylaalonio *store Jk was of interest to the authors
to extend the limits of katoAyl&tLon of the aompows" with
a movable sothylex-and nothenyl somber. I?Irot the &Ahors
investigated the k*tovlAylation of the e-alkylaost"astio
eaters described In this papers Based on the experience ool-
looted Ottf 4) on the conversion of the P-chlororlaylketoses
vith aestosoatio eater In the presence of potash in boiling
toluene, in the presence of only one sovable hydrogen atoso
Card 1 A4L secondary processes could U sialuded In the jcos*nt case.and,

30/79-28-6-15/63
The Conversion of O-Chlorovinylkotones With P-Dioarbonyl Compounds*
To Ketovlnyl&tion of a-Alkyl Acetosootio Isters
the sole formation of products of a normal kotavlaylatIon
could be oxp"ted* In the conversion of P-ehlorovisylkstonso
with sodium derivatives of the a-alkyl ac*to"etio esters
in tenteno the hitherto unknown
-acetasootic, eaters war* actually obtained without dlffl~
oulty and In good yIslds3
XCOCNne'0101413cocnlcooy 5 1COCff=MC3C_COOC2x5
2-01yo2sto 357 RISC 2HVC 409 COCS3
Owing to theacoossibility of the initioa substances and. Its
simple method this reaction to a oonvoniont method for the
synthesis of those interesting and such promising ampowAso
They &to high-boiling and stable oils which, however, easily
resinify In distillation In an Insufficient vacuums Their
structure Is proved analytically. The r*sultlof the brdra-
tion of *ns, of the** compounds points to the presence of a
doutlo bond in the ketovinylation products, which fact is to
to proved further by conversions* There are 5 reforenceal
Card 2 5 of which are Bovi*to

AUTHOM Koohetkov# X. X., Eudryavbov# L. 1.
TITLE: conversion of P-Chlorovinylk*tones Vith P-Dicarbonyl Compound$
(YzalmodoystTlyo P-khlorvlnilketonoy a A-d1knrbon1l#nyu1 soy*41-
noniyami)VI.Tha Synthesis of Some a-PjTons Derivatives (VI.
SIntes nakotorykh proizvodnykh a-pirozov)
MIODICALt Zburnal obabohey kbimit, 1959, Vol, 28, Nr 6.
pp. W1 - 1516 (USSR)
ABSTRACT.,
Card 111,
Recently the authors have olaborat#d a convenient method for the
synthosle of a-pyrones- The p-ohlorovinylketon# dissolved In
toluene Is &44*d to the magnealumetboxymalonic estor which must
form in a very small amount of alcohol. After the reaction Is
finished the complot*ly homogeneous mixtur* Is decomposed by
eans of glacial acetic sold. The 1-ketoalkenylualonic *star
ormed an this occasion Is oyclized to Q-pyrons without purifl-
;
cation by boating with acetic anhylrldo. The acetyl chlorlds used
In place of the anhydride yields sozewhat b*tter results ($to
the mentioned reaction saheno). A closer Investigation of the
mixture as carried out In the synthosis of the propyl-hosolog
showed that besides the pyrone product with & noltlng point

Conversion of P-Chlorovinylkstonoo With 0-Dicarbonyl 3Z1179-28-6-i6/65
Compounds. VI. The krnthesis of Bone a-Pyrons DorivAtivos
104-104,5 0 in tormod in a stall yield Its analysis
points to the composition C 9 0 . The fornation of minicus
A7
Ag l
ynthesis of other hosolocso
t
side products showed also I
which fact# however, does not hinder the direct separation of
pyrono from 0-chlorovinylkotone (44)- This way 6-9h$nYl-,
6-propy2- and 6-hoptyl-3-carbothozv-a-plrones were synthotlztd#
the latter two for the first time. Thus thin method turns the
6-alkyl-3-carbothoxy-u-pyrones Into easily accossiblt compounds
of vh1oh some are to serve the authors for investigating thou
as to their physiologic activity# nothing has hitherto been known
about this In papers. There are I table and 4 refsronass# 2 of
which are Soviet.
ASSOCIATION; Institut farmakologil I khiniot*rapli Akadtall nodItsinskikh
nauk 8081 (Pharmacological and Chemotherapeutic InstitutS Ac&4*vq-
of Medical Sciences USSR)
SnUITTn.- My 27t 1957
Card 2/j,

Lochetkovg .4, Koo Khorlin, As Yes,
n-.,tv at I gn t Ion in the foornsol Seri*@ (Iselflevvnivt v r'v
17.0ke"%O1.0 Vjbi)n the ',, `-nthei4is of the 5-."ut-tituted ;z-~x%vt0i
(VI&O dintf-ge 3-zamashchonnykh tioknstoloO
S".hu rn n1 obuhahay Ithir ! i , 19 58 # Vol . 28, Nr pi .. 1114'
Cne of the mopt alople metho4v of thl~ 1,yntheoin of
tho reaction of 0-chlorovinylke'soner vith hydroxy4mine,
NRn r,~vllzfd by VnchAt~ov unj hig Coll'borattkrs (ilefp it
it ts, hoveyerg nocoxponiad by two evnr,,!t1no* vira
the forositlon of tro 1740moric LnJ 5-30;TtItutTl frlvftzol~,,
Kochatkov further ahortai (1!ef that tho
ketaneq with hy4roxrlumiue cqure to form Pructieully ruro
5-vifbatituted isoxazole, en4 that the
vinylketone reacts undor the forration of 5-chlororgothy"
isoxazole-This fact provP3 that in th13 caie the nuclearhA*11v
nttark of kv4roxylsaino t"kei plre- at the cabonyl orroup %z-
cording t*hri : vche,4o meritlunqd. To Onlain, this problem th4
"utharip Inve4tiguted Oe rpaction of il-ohlorethyl-O-chlcrr-

7 9 7 - A 6,, f. I
in thoi Troxazol 'erierp 111,,"'n t1r, -'y-1thv!?i!' of t~e
Ad "'soyp"Zol
viny ketnn* -olth hydroxylamineo It tt,rned "t that the syn-
th*ols of g-ablorathyl-0-chlorovin.1 ketone, as well at that
of tte alraa4y knovn, doos
not meqt %1th any difficultion (according to the eptheyi son-
tionid in rpfer*non A*. In the conlener4tion o" the I-thlor-
ethyl-il-chlorovinylkvtopp with tkydroxylaminp the I-chlor-
Ahyllilustol ifts obtfitned in gooi vield (pithojt ony forna-
lion of dopoaltq) in itc treatment with sodium b1coholats, no-
e00,11"p, to Clato*n (V1hy%pn) ("of This indicaten a
A-nuhatifuted Imomqr:
~'H OH ---,w CH CRCI
I" H
,n the ro!k.?t!ons of the .-cblqolkyl-ti-chiervinylke*,onea *11th
h--idroxylftmine b9st4ev the oxtsols Oso scull scounts of
!~,-irub3tituted inomerr nkrz~ formoi. The LaynthpAia of tho
j-PIL111soxazols by thr r~t4uotion of the ccrr~?np,)nd2nr,
chloralkyll"oxasols with zinc -just van elaborat*4. There P-r-i
referen--ps, 6 or which are Soviet.
v I

AUTHORS: loahetkov# 1, 1, truchonkol 9. 1. $0T/7)-28-6-52/66
TITLX: Several pJ-Diarylethylamines (Nekotortye pj-diariletilaniny)
PERIODICAL., Zburnal obahchey khinii, 1956# Vol. 28# Nr 8#
pp, 2252 - 2257 (USSR)
LBSTRICT: The high pharmacological activity of the derivatives of
the allphatio-aroustic amines is sell known. ftyoral of
then are ingredients in medicines. A I&rG* and Important
group of the## compounds &r theto-phonylethylan1no deri-
vatives and-their homologs :ith ranah*d chains. In &441tiong
there Is nothing reported In publications on the physiolo-
gloal aotivity,of the Pop-diarylothylaslass, Son* of the
cyclic analogs of those compounds which contain piperldins
nuclei exert a strong stimulating effect on the central
nervous system (Ref t)s The author was Interosted in lnv*~-
tigating the pharsecological activity of several PqP-dI-
arylethylasins clerlystives as well as that of the 9-alkyl-
090-diarylethylaulnes, Their syntheses were carried out
according to reaction diagram 1: tbo 41&ryl&c*tonitri1*&
Card I ware, obtained by the condensation of brosoarylac*tonitriles (1)

Several POP-Diarylethylamines
307/79-28-8-52/66
with aromatic compounds In the presence of aluminus chloride.
Two of these, the phenyl thoxyphenylsectonitrile (11,
.C 5 ~~Os
Ars,06851 Ar's p, and phonyl-p-chlorophanylacitto-
28 OC6114
nitrile (11t Ar- 0 6BY Arl a P-CIC68 4) are descrtb*4 for
the first tiuss The reduction of the diarylsootoal trills
was carried out by catalytic hydrogenation at 45-709 and at
440-70 atmospheres over a nickel skeleton. A series of
11-alkyl-POP-diarylothylamines were, synthealsod In this 4&y-
Yor the monvalkylation of the 0,0-diarylalkylamines,
m*thylation vith the methyl Iodide of tho correspondine amino
was carri*4 out* The monoalkyl derivatives with Metter
radicals were obtained by the catalytic alkylation of the
primary amino* with alcohol* In the presence of a
skeleton, There are 4 tables
and 6 references,,
nickel
Card 2/
'k

AUTHORS: Xuaherovat go ?., Yovdakov# 1. P.# SOY/79-20-7-53/64
Kochetkovp 1. K,
TITLX: Indols Derivatives (Prolsvodnyys Indols)Y.The Synthesis of the
Dimi-Quatornary Ammonium Salts of Baratta (T.SIntes ble-chet-
vertiohnykh ammonlyevykh soley garaina)
MIODICAL: Zhurnal. obahchey khImilt 1950, Vol 28, Nr 7,
pp 1962 - 1967 (USSR)
ABSTRACT: The recently published articles on the physiological activity
of the asymmetrical blo-qualornary ammonluz *&Its (Rafe I-))
point to some prospects of then* coapounds with r*gard to DOV
gangliolythio and hypot naive preparations (gangliolitiaheskiyoo
gipotentivny.v* preparat;). For this reason the authors carried
out the synthesis of sione compounds of this group# using the'
acesesible alkaloid haraine as Initial product. The compounds
obtained vere of a certain interest as on the one hand just the
ble-quaternary *a.Its of the O-caxbolines proved to be &are
active, and on the other hahd haraine itself displays hypotonsivo
activityp as is knownj The compounds of Seneral type obtained
Card I are mentioned In scheme 1. Bitaldon, tlk* authors by the conversion

Indole Derivatives. V. The Synthesis of the Bis- SOT/79-28-T-55/64
Quaternary Ammonium Salts of Harmino
of harmIn* withAibromothane synthesized the symmetrical bis-
quaternar.y salt, the compound (VIII), as wall as the sono- ~
quaternary salts of harmIne with b*nsylchlorida, and the con-
pound (IX)o The synthesis of the asymmetrical bio-quatornary
anzonium salts *f.the harmine series was carried out in two
wxyvi 1) By the reaction of harmin* with dialkylaninalkyl
halides and & subsequent treatment of the reaction pr*4uots
with the halogen alkylt and 2) by the reaction of haralne with
W -halogen alkyl ammonium salts (yield 55-75%). The d*pandenas
of the Wotonsive effect on Via stricture of those dompounds
in discussed. there are 7 referenceso 3 of which "0 Soviet.
ASSOCIITION: Inatitut farmakologit I kb1a1ot*raVii kkadenil m*dits1nsk1kh
nauk SSOR (Institute of Pharmacology and Chemotherapy of the
Academy of Xedical Scioncos)USSR)
SUBMITTED: May 27# 1957
Card 2/3-

AUTHORS: ludr7ashov# L. too Kooh*tkov, N. K. SOY/79-28-7-54/64
0....... ...
TITLZ: P-Aninovinylkstolftes (0-Aminovinilkotony)IX. The Salts of
Trialityl-(Iokotoslkonyl)-Assonium at Ketovinylating Nadia (IX.
Soli trlalkll-(I-katoalksoll)-aanontya kak katovInIllruyushchiy#
aradetya)
PZRIODICAL: Zhurnal obshchey khlail# 1950# Vol 20t Or 7P
pp 1967 - 1969 (USSR)
ABSTRACT: Continuing earlier papers (Sets 1-6) the authors hoped that the
salts of trialkyl-(y-k*to&lk*nyl)-mmonjun could turn out
preparatively as convenient katoyinylating sedlap :I.9. that they
were capable of substituting In sons, cases the 0-chlorovit7l
ketones used In earlier syntheses (Refs 7,8). the authors lnv*#-
tigated the condensation of the eblorides of trI*thyl-(A-butyroyl-
vinyl)-wmantun. of triethll-(P-boo2oylvinyl)-a=onlum and of
trinothyl-(P-butyroylvinyl)-amonium with othoiy nagnestun salonid
,ester. The reaction took place under the addition of the solution
of the quaternary salt to the alcoholic solution of this *star,
Card I I.e. on conditions close to those of the Kannich (Unnikh)
P-Aminovinylketoneso IX. The Salts of Trialkyl- $01/79-20-7-54/64
(y-k*toalkdnjYl)-As2onius1&s Istovinylating Media
synthesis. The Initial product of the reactiong I.e. the y-k*to-
alkanyl nalonto ester cyolitod lace4lately on Its transforeation
Into the pyron* derivative In the tt,*raal way, or on the action
of acetyl chlorid#.(Ref 0). The 6-4kyl-3-carbethoxy-a-pyrones
obtained were indtntifl*d by saponification (Rof 9). The con-
denaatlon thus took plaeg In a corresponding way, however* lh A
Pmaller yield, Although the results are of no Interest In a
preparative r*spaot they are worth mentioning In principle
since they point out the fact that the salts of trialkyl-(I-kato-
.alkenyl)-annonlun# just as the Nanniob halogenalkyl bases, are
capable of having their ammonium Croup substituted in typical
nuoleophillo substitution reactions. There are 10 references,
9 of which are 3oviot.
ASSOCIATIONt Inatitut farmakologil I khtsiotitrapil Akadeali mditainsklkh
nauk 8931 (Institute of Pharmacoloey and Chanotterapy of the
Academy of Medical Sciences;USSR)
SUDMITTZD: May 27 o 1957
Card 2~1'

loamy,=# '*'*I VUMWAO X0116
e~
Toricus IfJpwwrUV*I- -ehloroproplau"Idose ftsr,,*b*khIv*
23 noo9s23"44w-S s5t (NM IISIO
I# tustitut fornk61441 I IftWotenpil AW =M
(Adds@)

SU RTA3901, L.I.1 90CHUMp I.K.
ftatbools of dietis sald* fro* L-pyronos. Shur.ob.khla# 28 so 91
944&2432 8 158. (NIKA 11112)
1, lastitut formakologil I khIsloterspli AM SM
("norks) (Acids, Orpolo)

AI~THORS: Kochetkovo go K,t Gottikht B. F. 307/79-28-to-25/6o
.............
TITLE: Reaction of P-Chloro-Vinyl Ketono With P-Mcarbonyl
Compounds (Yzaloodoyotviyo P-khloryinil':,~tonov a P-di-
karbonillayst soyed1noniyaol) VII, Acid Cleavage of tho
a-Alkyl-a-(3-Katoalkenyl)-Acetic Zst4ra ~7,'1'1. Uslotnols
ranshchopl*niye a-&lkil-a-(.-kttoalkenil)-atootouktuonykh
ofirov)
PERIODICALt Zhurnal obahchey khiaii, 1958, Vol 28, I.-Ir iog
pp 2732 - 2735 (Usn)
ABSTRACT: The a-alkyl-a;(3-k;toalkanyl)-acetic esters obtained
by the author (Re 1) by the keto vinylation of
a-alkyl acetio *star are of Int*reat for orranic syn-
thesis. The authors began their Investigation with the
reaction of their acid cleavage. Thom* conpoun4a are
related to the acid decomposition of a,a-diacyl derivatives
of the asters of fatty solds so that an easier separation
of the toyl group than of the 0-kotoylnyl group was to be
expected* The ole&Tag* of the
acetic asters according to Dieckmann (Hof 2) and
Card 1/)_ Douveault (Hof 3,) (MiczanqDuvo) failed due to their

R;action of A-Chloro-Vinyl Ketone With P-Dicarbanyl 507/79-28-lo-23/6*
Compounds. V11. Acid Cleavage of the a-Alkyl-u-(3-Ketoalk*nyl)-Acotic
Estero
tendency to complex condensations and to the for"tion
of aide products* The use of aqueous azzonla solution
with the addition of a-monium chloride (Hof 4) was
successful in this cleavace, with the above mentioned
eaters being subjected to a sufficiently oagy acid
cleavie under the forration)a-(3-k*toalkenyl)-alkane
acids See Reaction Scheme I . The more accurate testing
of this reaction by the decomposition of a-ethyl-a-
(3-ketobutonyl)-acette ester sbowed that the final
result depends on the amount of the related ammonia
solution# as It may be seen from the dnta given in
table It The reaction in of general characters It Is
shown that the acid cleavage with the increase of the
molecular weight of the a-alkyl-a-(3-katoalkenyl)-acatto
eaters demands stricter conditions and at the same
time offers smaller yields of a-(3-k*toalkenyl)-alk&n*
r.cids. There are i table and 6 references, 2 of *-ich
Mrs sovieto
Card 2/,4,

AUTHORS: N K Khocutova# Yo. D., soy/79-20-lo-24/60
TITLE: Investigation In the Isoxazole Series (Issledovanlys v
ryadu Isoksasola) YII~ Chloromethylation of Isoxazoles
(VII. Khlormatiliroyanlye izoksazoloy)
PERIODICAL: Zhurnal obahchey khimiiq 1958, Vol 28, Ir lo,
PP 2736-2745 (VSSR)
ABS71RAM Recently lochetkow showed that the 3,5-dinothyl
isoxazole can enter into the chloro=ethylation
reaction (Rot 10). Results are mentioned that were
obtained in a detailed investigation of this reaction
with various substituted Isoxazoles, The *--ithors
proceeded from the chloromethylation of the onaily
accessible 3,5-dinothyl isoiazolt, ,is It was the most
useful reaction and excluded the formation of Ino-zera:
Be-C-CH 3 ClH2C- C- C-CH3
1 1 1 1
H C- C N --- ), H C- C ~
Card 1/3 0

Investigation in the Isoxazole $#rise. VII.Chloro- SOV/719-2e-1*-24/6o
mothylation of Isotasoles
The chloromethylation was carried out with par&-
formaldehyd* and hydroCen chloride, dichloro dimethyl
etheri hortochlorc dimethyl other using various catalysts
(ZnC129 H2SO40 SnCl,) and various solvents (hydro-
chloric acid, sulfuric acid, dichloro-ethar*o chloroforn)v
The results are given in table 1. The reaction with
paraformaldshyde and hydrogen chloride In the presence of
zfklll2in dichloro-ethane as wall as W~t with dichloro
dimlAhyl other showed the bent results. It van denonvtr~.-*ed
that the easiness of the chloromothylation In the
aarias of isoxazoloo incraas*e with the number of
methyl groups In the nucleus. It turned out that
In all cases when the position 4 In the nucleus of
inoxasole In not substituted the chlorozethylation
reaction tends to that position, which alno holds for
the 5-phonyl isoxasolot A saponification method of
the chloromethyl Isoza2olas into the corresponding
alcohols by heatingr the chlorides with an aqueour lead
Card 2/3 oxide depositing as well an an direct oxidt.tion nothod

Investigation in the Isoxasole Series. Y11. Chlorc- SOY/79-18-10-24/60
methylation of Imozatoles
of the substituted chloromethyl Isoxazoles Into the
corresponding isoxasole carboxylic acids were d~v1s*d#
Tablo-2 gives the chloromethylation of laoxazole and its
hamologs, There are 2 tables and 18 rofer*nc*s, 8 of
which are Soviet.
ASSOCIATION: Moskovskly gosudcrationnyy universitet (Uobcov State Uni-
varelt,y)
SUBMITTID: July 29, 1957
Card 1/3

AUTUORS: 129UU=06~# Khomutovp H. U., S07/79-28-ti-25/55
Karpoyakiy, M. Y&.0 BudoTakiy, Z.1.
TITLE: Cycloner1ne and Related Con;ounds (Tzil-lonerin I
rodstyennyye soyedInoniya) 711. On tho Wntheals of
Cycloverine ( 111.0sintase trikloserira)
""burnal, obahchev kh1alif 19~0# Yol 20# Nr lit
PP 3013 - 3019 (USM)
A r, MMA C T Lntely# the Authors had reported on a new a;rntheala
of the antibiotic cyclocarino, the d-4-azino Isoaxazoll-
done-3# from an accescibla enter of the a,P-di-
chloro propionto acid and acetoxime (nof 2). As
further chemical And clinical InventiZationa (Rafe
3#4) proved itt high antitu'Zorcular actlvit7 thic
synthesin was Investi,-ated In 49%nil. All other
scientists have hitherto proceeded from the weakly
accessible amino acid of nerinet The synthesic of
the authors took place according to the a9ttioned,
scheme 10 with methaarylate serving as Initial sub-
stances The condensation of the methyl-aop-di-
Card 1 chloro propionate (1) with acetoxite zoems to be the

C;rclouerins -elatedCompouYids. 111. On the
of Cyclooarirc
bottleneck of this eynthents, !he difficulties ire
due to the fact thut a selective tubetitution of the
P-haloZen atoz must be carried out. The reaction (1)
with acetoxime wen Inveati-r--^ted with differcnt
solvents at different tomperuturva an! at diffezent
r:Aiou of the ro&cting conWounds. The condehuation
(1) with the ox1ne supplied the bezt reDults in 0the
proseroo of rodium nothyl-Ite In nethpmol at 0-5
(yield of compound (11);25-30~). Dealdoo (IT)
nloo the a-chloro 0-mothoxyproylontto (20%), rnd
a;parontly also the noth71-a-chloro-acr;1ate were
obtained, Of the two poncible reaction proceavea the
one with the previous separation of h4droCer, .nl!le
with tho nubnotiuont affiliation of the forn,~:d a-
haloGen acrylate to the double bond w-3 solecttd.
In the aQinstion the otter v-.9 firtt tr.~.7-forrod
with ull:ali liciuor Into the acid (M), whi.-h then was
subjected to the aninntion. 14*".or lo!,:or ex;erlnorts
the ami-lation van cnrried o-4t with excess liquid
Card 2/ ummonia on heatinC under th4o for-.atlon of (IT).
I

Cycloserino and Related CompourAs. 111. On the Synthosta SOY/79-20-11-215/55
of Cycloserine
Thle acid (IV) vas separated In forn of the
chlorine hydrate, which further on served as the
main product of the synthesis of 41chloro h1drato
(V), The &old hydrolysis was used (Schoje 2)-for
the selection of a secure and convenient transition
from (IV) to (V) under various conditions It was
found that the synthesis of (T) to most convenient
from (VI)l it may how*v*rj also be carried out
directly from (ZVI or (VII ). In the last stage
it was possible to increase the yield In the
cyclization of the dichloxins hydrate (V) to the
cyoloserine from 65 to "l %1th the product already
separated In analytically pure atate from the reaction
-aiiturso Compared to *arlior syntheses of cyclo-
sorlne the one mentioned hors offers a better yield
and-avoids the use of resinous compounds (Refs 5,10).
The racemate of cycloserine showed a high activity
against Infections of all types. Th*r* oxe 1i refer-
Card 3/ oncesi 3 of which are Soviet.

Kocbetkoy# No Koo Kudrynahoy, L. 1. SOT/79-20-11-26/55
TITLE: T;;~~~~ronoa. Synthesis of the VInylogs
of the Eaters of P-Ketonio Acids (Novaja reaktaiy& a-pirotov.
$intozz Ylillogov efirov P-kotonokinlot)
PER10DICA:.: Zhurnal ObshoneY khImlit 1950# Vol 23, r~r 11,
PP 3o2o - 3o23 (USSR)
A29TPACT: Continuing the pa;ers by Poohrmnn ~ Welsch and
Unuffmann (Sofa 102) the authors report o,i a now
reaction vf the opening of the a-pyrone cycle#
which made possible the synthesis of the hitherto
unknown vibylogs of the enters of the 0-ketonic
acids, On the action of annonla or aro:aatle aninas
on the asters cf the 6-alkyl-a-pyrons-3-carboxylic
acids no an1dot (Ref 3) are forned. An wqatable
~produot is.forred fro2 the 6-cothYl-3-carbethoY4-a-
pyrone and anIllne in benzene solution# the antilysis
and nolocular %;eia%t of which point to the affiliation
of one molepilino to one mole enr'.9thoxy -,Yrons,
Card I which is opposod to the otr%&otura of mn anilids. The

A New Reaction of a-Pyronso. Syrx-,oztv of cie V1rn,#1oza SOV/79-20-11-26/515
of the Eaters of P-Ketonio Acids
further experiments pointe4 to the preaerce of
a free carboxyl group and to lain* bin0trz;. T%tia,
It Is clear that In the treatment of cartethozy pyrone
(1) (RoOR ) with aniline the pyrone cycle la opered.
In careful dsoarboxylation of the reaction product
(1) with aniline tho,;t.%yl oot*r of the 1-11-phanyl-
aaino corbio sotd (I ) is obtained. the rtnictur*
of which In prov*d by way of t%e o~tnv Iq-1rolyals
by the tranefornatlon Into the vinjploi; (IV). no
dosorlb94 now reaction of the o;*nItc. of the
a-pyrone ovole to of Cenaral o%ornctcr. Thus# U's
pyrons (1) (ftzC,R7) with aniline in alcohol tolutlon
yields the ' ;0 compoltn'd (11) (a. C387) which by
decarboxylation and hydrolysis with 4droobloric
acid yields the compound (IT). The syntliesizA vinyloCs
of the P-ketonic acids traneformad into the enters
are colorless$ ruffictontly atable liquids that 4darken
only In the course of tire. Thlere Are 5 referonces,
Card 2 of which are tovist.
2oat sizi-le alkyl-P-cbloro-
vinyl ketones, at these can be obtained nor* easily
b,Y the first mentioned method. In the came of a
Card I fjL1lure Of the first method the aecond z&y be of

Synthesis of Aliphatic O-Chloro-Vinyl Xotonee From Sol/79-28-ii-27/55
021-90thyl Ketones
Importance, Two examples of the synthesis of the
allphatla-0-chlorcovinyl ketones from ory-nothylone
ketones more givan, which can In all cases be used
for the allphatia series an well, The reaction of the
oxy-mott4lone pinsoollne with thlonyl -.hloride
in benzene solution was Investigated in detail. It
was found that the substitution of the onol hydroxyl
of the oxy-mothylone ketone by chlorine taken place
sufficiently *asIly'#'In this case the yield of alkyl-
p-ohloro-vinyl ketones amounted to 70-80%t which must
also hold for other -Ilkyl-0-chloro-vinyl ketones. The
earlierinaacessiblo a-alkyl-P-ohloro-vinyl ketones can also
be obtained according to this mothode There are 15
reforenosel 9 Soviet references.
ASSOCIATIONt gookovskly Cosudarstvannyy universitat (Moscow State
Univernity)

AUTHORS: Khorlinp Ao Ya.p Chishovp 0. S., SOT/19-20-12-41/4i
Kochatkovf Ws K,
TITLE: Derivatives of Bicielo (1,2p2) Reptano (Prolsvodnyyo Mtslklo
(i,2,2)j;*pt&n&) IT. Some Amines and Amino Alcohols of the
Bicyclo (1,2,2) Roptan* Series (IT. Kokotoryyo axiny I amino-
spirty ryads bitalklo (1,2f2) aeptana)
PERIODICAL: Zhurnal obahchey khtaii, 1950, Vol 20, Nr 12,
PP 3345 - 3351 (10332)
ABSTRACT: The anineq of bloyclo (1,2t2) hoptans, series ovIng to the
physiological aotivity of nome of their most Important
compounds are attracting the attention of scientists (Rafe 102).
The authors had recently described the synthesis of see*
amino ketones of this saries (Rof 3)9 nazoly, the synthesis
of some deriv.%tivas of 2-acyl-3-dialkyl 4minobtaycla, (1,,2,2)
heptane, To continue the invostiptinn of the phystologicul
activity of the &mines *f the bloyolo haptane series some AsinO
alconole and amines of this series were synthesIs*dt which
were then pharmacologicAlly InvestieAted In the form of
their bydrochlorlies and iodine alkylat*s. It was Inter-
Card 1/3 esting to Investig4to In Vhi0h way the physiological activity$

Derivatives of B1cyolo,,(1,2j2) Roptans. IV. 3ozo Aninos SOY/79-28-12-41/41
and Avino Alcohols of the licyclo (1,2,2) Heptane Series
especially, the h.-potensive effect sight change In compounds
with the amino group in position 3 and with the *a" carbon
skeleton as that tD be found In bicyolo (Ij2o2) h*ptanot
if In the position 3 an oxy-alkyl or just one alkyl group
were nubstituted for the acyl radical. To arrange the trans-
formation of the amino katones of the bloyclO hoptane
series into the corresponding amino alcohol* their reduction
with aluzinum-lithfun hydrld* (LIAIN4) was carri#d out
(Scher@ 1). This reduction takes place very astly. The
lelds of the corresponding ^min* alcohols M. (11), and
111) tin- vwn7bv-for* "r*-jklu it quantitatIve. Tbus
~
alkyl 3-dIjakyl--:sn1nob1oy*l* tt$212) hmeptmw mm
by reduction of-2-acyl-3-41alkyl blqyolo (If202) haptane
with UA19 V 2--alkyl-3-dialkyl am1do bleyelo (10202) haptanes
were obtained In 990 WAYS: 1) By treating 2-40YI-3-4162kyl
amino btoyclo (1#2,2) hoptane with phosphorous p*ntaohlarldep
by further reduction of the Intermediate products with
tin* dust, and by hydrogenation. 2) By treating 2#1#-oxr-
Card 2/3 alkyl-3-dialkyl-azInobloyclo (1,212) hoptans with thionyl

Derivatives of B107010 (1t2j2)R&ptan~. IT* Some Amines SOY/79-20-12-41/41
and Amino Alcohol* of the Blayala, (1#2#2) Reptane Series
chloride and with subsequent hydrogenation. The problem
of the dependeno* of physiological activit on the strueturs
of the amino derivatives of bloyclo (192,25 heptsue Is
discussed, There are 4 referencesp 2 of which are Soviet#
ASSOCIATION: Institut farmakologil I khtsioterapil Akadeall maditalaskikh
nauk 333H ( Institute of MrMooloy and Chemotherapy of
the Academy of Xedical Sciences# USSR
3UBMITTED: September 30t 1957
Card 3/3

AIV,'L,0?31 Doubrovikaya, V- , Pentill, Tu- A%- T,amixtyp
TITLEs Ple Invuatlia tion or Vitt .", w I 1.~; i OC tl-,: Al".-I -LQA,nO,?Injl
Katonz,,z Accozdln,; to Irrrar.-d Ab~~>rjtii.n Ida
tautu-~,jril
(USJR)
PERIODICALi ZhIAXTUI ViZiC1,QJ'-Oj r1l'AHO i"dj 101. 37, ;4'1' It
ABSTRACTs 'Pisi rr,~jvnt vor% ii directl-, cornec'.;vl -iz'~ worka (rate.
rencl- 1 and 2)s -Pw i-ivc.,&tI,-a-t1ow4 In fcr.,.o mforrad to the
clarifick.Lion 0; 11.vatl on cr th-, Of LWi.4no-1jIJ9-
-wiltojerija, Tbk, pruzs~.mt jork i.- -1co tt~ 3.16e question.
'Pie C012-
;~,O,rod with Uach 006r. I) Vh~; rtrzo 2:,00 Gf tho VAL-
lanoc-X-H-oj,3111atIovj- In thii c: vlld
vin,il ketonal iac* ir, O'c M-for~~, 4.1ij
'1140 and 22 0.1- I.Le (,:3cillatlons of
th, .0 #1 .. -;
thfi OH ,roupt are prticent. It ii j,,own 0~ at-forz 1; a acre
or loan pure luide-,~ncl fom,
';to vin,:0 I '5L - 17cc 0.-4- of Vic '.un"I. All lata obtain-
Card 113 ad 1wro ar..-a% In f-imir of V%Li f4,lt V~ t c4 -form curr4jponds
Now-
,~Tl

-2(,132
Pie Invt:stl,,,Aticr- o~ tb4~ lautci.4iri3 i of Vie -A ACCO.-d1nil
to Infrimd AbjurptA-vn Spz?ctra
to tl,,a Laida-aiicl 916 t;m# c.;d ttat 14%z 1,,roduct of Vw
c4 -fur;A z_tA Via -JiVac of the &X - r* p a u r % a ..%
Of VW 1~31'N-IIAOI- 1111i fIC ~,lic ~.i, .,d:7 3) Aht
I , % -.1-: 0' tLe
nin,lc I 'C - 11150 0,,- 1, ~!10 J~-.:Ct "At. :I
And f-lcruj of tll;~ IC02 C"
b~,r,d za rt. p rj ion t , u A c-L f n z;-,~ c t run 0 f the
OL-form ard ara 0,nractcriatic fl,r 1:,, i~
rip la I ly intcv~it4tion cC tl_! re, dif -
f icult, 4) aw T"r,)j;u 70,- cn- , In Chu luix-
L Q Of cL - mid ('-f j)'_.jZ 0 - 11. ir._'~'11_";W.J~fj"C
. - -I i -14. -t- - ,a "re Ire-
,.,. L n Adc in . C ,
.ILI) LPit J:; Lula lj~ c~Di;c _ i jortl 11 13 'Tt~r, ~Jvg it, tbc apetra
cc-rfa:34 It il r~~uvaw-j to the
-i
.9; fur-a'. Its.
It i._;~ that ~lj 1, r.-- i'rj -n .-Ith rczpuct
to tht oti4ar
iL Lj v- 11: oru t ion
(in C
vin.,l ',titellu, -if ita In llf-
u;Aut
&'ormnj -viz. _r,
C.dre 213 in r.i fA) -nj &Z an

Invoatif-ation u" the T.Auto:ssrI;;-,, oi 1khe ;11:. I-C-A-Anw:ItijI -'ecorUz,;
to itirrarcel Ab~,ori,'.IQn Jpsctra
lmidt-ct.ol-fora "3), *".crc un~ I C of
%
wIlAch are Slavic#
ASSOCIATIOUs Lioicov Jt~ite VnIvarelt., i-un! 9. V. Lo:,-.orujoy
,(uOv%CV,;%1,7 univeraitut In. '"'. V. Lo-,iorwrva)
M4141TITEDs OCtobc-r 2.11 In'55
AVAILI.B=t Librar;/ of Ccn(;rcs*
Card 3/3

!.;~40". x0chetkov, .1. K., !1if&AtysV, Fa I*. S37/20-121- 5- 1,1147
t
k
T'T',~;- :.;obstitution Rejactions In tho Unthylen* Group of P-Jroto-
acetals (ID r"aktaiyakh zameshcheniya v mettlenoTon %Yen*
L -410`1 C A L Doklady Akadewli nAuk 929R. 1958. Vol. 121, Kr 3t PP- 462-465
WISH)
AROITRACT: In recent titea f,ketoncetals hnve been =ore ani core widely
Opplied in~orgunia s nthestv, 'it to trqv that they are easily
t -atonecUle recently prodtictd
actossible (Peru 1 31. Cyclic ~,l - %
In the Ipboratory of the authors turned out to ba particsilar-
ly al,vantageous becaute of their hirh stability (Rof 4).
Hitherto only thQ conlonvationa wtt't ree,-cct to Use koto
roup of ucetalt have been -ased for purposes of synthesis
fRefs 2, 4-6) or thqA,r tranaformationc Accorfln;, to I*h#
type of reactivnr of A-dirarbonyl tompounis. This was done
rclic compounds
mainly for purpopos of synthesin of heter-:~c-
(e~g- Refs 1, 7). Th~7 reLictlon of rt-~I:icn!!tont of ~-kqtoncettAx
in the methylvne group In of in',etest eince Jt
will ren4er potitible their np.,linntior, in L ccupletely new

'~;ube t i
tution Rf-nctionm in %he Yethylene nrpiq of
field. Prelininnry *f Indini.7a concernin,.7 reiketions of thio typo
gre reporte4 on, e) bromination of 1,1-keto&cotale unier verlous
conlitiona. The mothylone member can be easily brozinated '~n
the aquDous medium In the preoe".# of barinc carbonate, 7hc
ronction becomes, however. complicated by the clatavage of
the acetal Kroup. Thus moso-oubatitutiA S-ketouldehyden arp
formed. A more interesting result was obtained lin the cas-r,
of bromination of.cyclic acetals In other In the presence rf
bariumcarbonate. The saro bromination tukes plecal the
aoetal group, however, in maintsineC The obtained brozinr
acetals ctri be further used for difftrent Furposes. b) One
w' ilia most Interesting possibilities 12, however, theAe-
brominntion in besizene under the action of caustic patash.
In the case of action pf an excess quantity of alcoholic
rAknli upon moso-bromine-ketoaceta's 1-keto-acil-e%her is
formod an a renuit of k further transfornatibn of O-acttjl-
~eton--Ocetal. 0 1 further reacticr. i9 bqln-,,r Inveptigti'ved
-61, the itithorn~ o?_A~tlon by me%nn of liad tetru%mtate~ it.
lizethyl acttal
,vitli this. rerigvn-z in t, benzene- or sArrtouc aol-kition ficetRI
is ox-14titel on Uhrinethy] .'hp reaction becomos ror^
1 .1i0 grollp.
Card 213

Substitution e;.ctionv in the Methylens OrDljp of A-Yetoacotals
complicated by replacing one of the alkory radicals by the
acetoxy group. d) Furthermore the condeneAtion of the eyelid
bentoyl kcatiLldehyde acetul with benzaldthyde was Lnv*sti-
gnted. There are 12 rQf0r9n0Q3j 4 of vh1ch are Soviet.
ASSOCIATION. 'rookovakly gotudirstysanyy universitet In. 1% V., Lomono-ewft
(a-oacow s1tate tiniversity Imeni X. V. Lomonovov)
PRESESTM F D Varch 10, 1950, '0Y A. If* Yeameyanov, Ulembor, Academy of
"'cienceg, USSR
3 U B11 1W i, DV&rch 3, 1?58
Card 3/3

5(3)
AtITHOW. Shoynker, Yus N#j Aftbrushr 1viviij
Koahetkovp 1. K,
TITLE: Acid Propertlesof 3-Aoyl Pyrazoles ( 0 klulotnykh evoystyakb
3-atailpirasolov)
PERIODICAL: Doklady Akademil nauk "J53n, 10509 Yol 1219 Nr 4,
PP 7o9 - 712 (U351.)
A"TRACT: 3-Mayl pyrasolas !Ave properties of wank acidn (20f 1). TO
explain this the riuthorn asetimed thit tht? n-,It fortation is
gocoapanl.94 by a tautooorie displaceient of the double %code.
The aronatio pyrazole myoten to ruppoted to be disturbed and
0-astal derivativcs forred (Scheme 1). The well known thtares
that the oxygen aton Is more ntrongly than the nitrogen
stool which cau-~*s the naMtive charge to be --wainly concentrated
on the olygen atov, tends to kroy* this. An oarll*r Investigation
(Rof 6) n the 100ratory of the nothors hits shown thAt In
the ultraviolet bp*atra of 3-acyl pvrazoles on tho trnnsition
from n neutral to an alk"llne nodiun a c-moideratle bathq-
chrotelo displacerent occurs. This tend to show charges
Card 1/3 of the system of i-eleatrons of the nolecul-. Witb 3,541-

AcId Propprtion of 3-Acyl Pyrasoles SOV/20- -2.5-4-38/53
phonyl-4-bromo P7razole which In also acidic, but incapable
of the above tautonerie dIvel-Oo7ient, no di-placesent In tbo:
apootrun ocau"d (Rof 7). A ioconi poanibility (Schene 11)
of the noldity in question ic that the 9-9 bond in the
pyrazole nucleus Is polarltei# which -WI-en ioialblo the
separation of hydrogen an proton. This nny occur due to
the action of the #lectron acceptor errvct of the carbonyl
croup of the acyl rniical linked with the nuclei* (Rats 0,10).
After the first oxk1nnation (R~!f 6) hn! not nide ponvible
a definite choice 19twoon ache-to (1) nnd (11)j the authors
investigated the Infrare4 spectra of the ac:l pyrazoles and
their -aetal derivatives. Figure I gives the resvlts obtaln#4*
They cauned the authors to eoniolately dro; the asnumption
that the salt formition of the apyl pyrazolea let4iag to
the formation of 0-metal derivatives (Schone 1) take PlUces
In connection herewith Ono 'the a.~jrllor anx,;nptlon (;Of 6)
of a tautonerism of the ~-acjyl railcm1a in 4roppod. It be-
comes clear that at, far an Chore Is a carbonyl -roup in the
metal derivatives of the 3-acyl pjrazoles tho sAlt forastion
of thane compounds Is connected with the polarization Inareaso
Card 2/ 3 of th+- H for:iatlon of the pyrazolo noolrus unior the electron

Acid Properties of 3-Acyl Pyrazoles SOV120-123-4~-51153
acceptor effect of the acyl group (Sohome 11). Apparently the
disturbance of the aromatic pyrazole nucleus, In spite of the
high electronegatIvIty of the oxygen atom, represents such a
great binderance that salt fornation with the nitrogen atom to
an energetically advantageous process. The mentioned batho-
chronic displacement is probably connected with a certain de-
formation of the system of a-electrons of the pyrazole nucleus.
This in also proved by the abovo-montioned displacement of the
bands of the Cow 0 group In the spectra of the 3-&c,11 pvrazolo
salts* There are I figure and 13 referenceo, 5 of which are
Soviet*
ASSOCIATION: Monkovskiy gosudarstvennyy universitet In. V. V. Loaonosoya
(Moscow state University 1nont go To Lononosov)
PRZSRNTXD: July 1# 1950# by A. No Nesmayanov, Academician
SUBMITTICD: June 250 1950
Card 3/3

1wromn 0,1 AUUM TA E%rMn8lstOrjs I rIT I , I.A.EtrousiswIl
5k"10 0,9o
Exaftatift with oomplai metal hydrides) Toest*AOTIGsls "lekBay"
g1dridenj gotollov. Nookwo. Is&wo inostrannoi lit-ris 1959o 912 p#
(XIIA l4a)"
(Roduesions Chosioal) .(Rydddoo)

5.31100 1 ~ef,I
sov/63-4-6-31/37
AUTHORSt Kochetkov, R, K., Nifan't,yev, E. Ye., Shlbayev, V. ff.
.. . . ............................ .
TI'A"M of COMMInIcations. New Syntheala of Phenanthrene
PERIODICALI Xhimicheskay nauka I promyshlonnostl,, 1959,p Vol 4,9
Mr 6, p 8W tuSSR)
ABSTRAM A now method of synthesis of the phenanthrene ring
system was developed. The above aethod allows ob-
taining 10-alkyl-1.20 p4-tetrahydrophenanthrene, and
9-aUqlohenanthrones hew oroducts) according toi
0 SOXI UWAi
AKIs VO
R Oil
CO4OVWj
i p-all
10-Al
Card 1/4 111
.*Brief Connunicatione. New
of Phenanthrene
Syntho~sli
SO*V/63-4-6-31/37
Cgolohexanone was condenned with acid chlorides In
t e preseneg or AICI 3 rorml acyl-2-chlorocyclohox-
-2-enea (11). R - CH 3S bp 11-1090/15 mm
n20 1.49%0 d 20 1.1232, In 82% yield) R - C
D 4 20 20 22A5
bp 102-10?/9 mm. nD 1.4929, d4 1.0903.. In 59%
yield. H9, bp 70 4, n 20 1.4859*
20 R - 'so-C4 -710/0' D
d4 1.01120p in 115% yield. The above compounds II
were converted with ethylene glycol and with alkali
into monoethyleneketals of 't"l-acy1cyclohexanones (11X).
Card 2A

Brlef Cormun Ica t Ions. New Synt'l.eals
of Phenanthrene
3
ASSOCIATION:
SUBMITTEDi
Dehydration of compounds V over rd rorm 9-alkylphenan-
threnes (vl)- R - CH 3' picrate, mp 1"5-1490; R - C211 51
p1crate, mp 120-121'.
Lomonosov Moscow State Univer-11.y f'M-skDvskly
I "
.gosudarstvennyy univeraltet imeni Lomonwl
M
June 91 1959
Card 4/4

a3w Ljmmw~d 0
.OfftSls WPOOSI Of &09 PrOdullcme Tost,AW SM 14 ao,ls&14
'590 (NDA 1232)
1, hatItIA tarfttOIOCU I khtstatampli ANN IM,
(no I is 11111 1
in 31agela(fto))

AUTHORSs JJqShAJkOX+_1&_L 9 Budovskly, 2. Z.# soy/79-29-1-16/74
Doomtoyp L X*# and 'Narpeyokly, X. YA.
TITLEs Cyoloserine and Related Compounds (Taikloserin I radstvennyyo
sorodift*6176)
M CK -Densoyl-Amlno Acrylic Hydroxnaide Acids (IT. OL-Sonsollo
sainoakrilgidroksamov"* kisloty)
PERIODICALs Zhurnal obshchey khimil, 1959, Vol 29t 'Ur It pp 68-75 (0391)
AIDSTRACTs In the search for methods of synthestaing thv recently dia-
covered antibiotic ayaloserln# and related conpounds the
authors believed It would be of advantage to extend their
Investigations to several hydrotiaido *aids having an myl
amino-S"up in the OC -position. Further resotions with this
group-brought about a now way of synthtsixing eyoloserine
analoguess.Thq present paper deals with the synthesis of
A -substituted cK_ben20yl-SA1AO acrylic hydroxaaid* aolds..The
most:ravarablp*-synthesis of those co2pounds was the "action
of asollAs" 0 1 with hydroxyl Wne. Shaw and XcDowell
(Rof 4) suaoseded In opening asolsaioiie by reaction of
2-phanyl-44bensylidene oxasolons (Is) with free hydroxyl mine
Card I4k In methanol# This reaction, was, however, occounanted by

Cycloserin* and Rolatod-Compounds. 50T/79-29-1-16/74
M cc-Benvoyl-Aaina Aerylio Wro2sulde Acids
telde-rosetions so' that the yield In cK-bensoyl;aaIno-A-Vh*ftyl-
acrylic bydroxodde &*it (116) mounted only a 50 %, Apart
from this sold proplonto
acid was separated (25 ~). Here# the reaction was carried out
under varying conditions, Of essential importance in this
.connection the optimum percentage of the sediust which to not
allowed to Mood 5-6.50 as otherwise complications would
arise, thus*& general synthesis of /S-aryl-ac-bentoyl-asino
acrylic hydrazaaldo sold* was worked out by reaction of
2-PhenYl-4-arylld9ne czatolones with seetto hydroxyl amine In
methanol (5-605 %1). (Yields 70-90 %) which to also applicable
to the synthesis of /5-alkyl- Ot -ben20yl-S2In0 acrylic
hydroxamilds aaides By attalytto kvdrogtnstion of,4 -aryl-
-0c -bonsoyloaalso acrylic hydrox&sIde acids the 0t -bensoyl-
;e4aryl alanine hydroxamide toldi were obtained. The
ature of the syntheelsod co;pounds was proved by
hydrolysis up to the OL.-bentoy -,A-aryl alaninss. There are
i figure# 3 tables. and 16 references, 4 of which are Sovle4k.
Card 24-

SOY/79-29-1-17/74

AUTHORS., -
Kochatkovp So 1.# KhorlIn# As Y&.# LopatInsp X. I*
TITLE: Derivatives of 31oyolo-(i,2p2)-H*pt&no (Proisiodnyyo bitalklo
1,292) Ceptwia) V, 3-Amino Isocamphano and Related Compounds

V. 3-Aminolsokamfin i rodetvonnyyo soyedinonlya)
~
PERIODICAL: Zhurnal. obehohey khImiiq 1959, Vol 29, Nr 1, pp 75-81 (USSR)
ABSTRACT: The authors worked out In detail the synthesis of the product
3-methyl-saino isocamphane vhlc~ van recently found to be
highly active (Rot 1) in order to obtain now knowledge coA-
cornIng the relation between the structure of the ganglion-
blocking and hypotensiv* proportion of a series of amino
derivatives of bicyclo-(1,2,2)-hoptano (Rof 3). For this pur-
pose they synthesized several other V-substituted 3-am4no too-
camphanes. Only brief descriptions of the synthesis of 3-mothyl-
amino Isocamphano by reaction of camphane with the poisonous
hydrocyanlo acid have hitherto been published. As found In
this connection the described reaction takes place in wo
directions at +50 (Scheme 1). At -20 up to -150 It proceeds
In one direction (Scheme 2) In which case the yield In 3-form-
Card I aside Iscoomphane amounted to moA than 70%. In order to avoid

SOV/79-29-1-17/74
Derivatives of BIoyolo-(1,2#2)-Hept&ne. Ve 3-Azlno Isocamphane and Related
Compounds
the highly-poisonous hydrocyanio &aid now methods of synthesis
of the,acyl derivatives of 3!,Aaino isocamphane war* Invosti-
gated according to RitterilrAwakove mentioned (Rofs 5t 6).
According to Vagner It was possible to substitute hydrooyanio
acid by aceto- and benzonitrile at low temperatures of up to
-500# In the condensation of camphene with dichloro- and tri-
chlaro-ace.tonitrile In the presence of concentrated sulfuric
acid it was possible for the authors to obtain already at 00
the compounds (lilt s-CHC12) and (lilt lb-cci 3) which lead In
the reaction to 'the compound (111), with R-CH3 (Scheme 3)1 in
this case the regrouping according to Wagner was not necessarye
The aoyl derivatives of 3-amino camphans, were used
as initial products for the synthesis of secondary amines of
this isries, The yields of the compounds thus obtalned M,
(TI),and (VII) war* very high. The results of the physiological
investigations of the above compounds together with 5-anina
isoaamphane are mentioned in the table which shows the
dependence of the ganglion-blocking effect of the structure in
the asries of amino derivatives of isocamphane. There are
Card 2/JL I table and 0 references, 2 of which are Soviet.

AUTSORS: Koch&tkoYj_N# t Torotnikov&# Lo A* S07/79-29-2-38/71
TITLI: Some Derivatives of 1#2#3-Tr1aminopropene (Nekotoryye prolzy*4-
nyys 1,293-trissinopropano)
PERIODICAL: thurnal obahohey khiaiit 1959, Vol 29, Ir 2, pp 532-5517 (9531)
ABSTRAM From among aliphatic-arosiatio amines many are known which 4*-
Y*Iop a strong and versatile physiological activity, eigo the
derivatives of X-substituted ethylene diamins of type 1). It
was of some Interest for the authors to synthesis@ the 1,2,3-
triaminopropans derivatives of type (11), which so far hav* bo*a
unknown$ and to investigate their physiological effect* Recently
Morren, Be and Denayerp 1. (R*t i) reported on the high spas-
eftolytia activity of some derivatives of this type,
R N / 1 RINCH 2'CR-Ca WRI
a / X-OH 2-CH 2-Y\ a 1R1122 (11)
2 (1) 4
In (1) RI and 1. are aromatic and allphatle-aromatle radicalal
R 3and R4 - oilY C2'5 etal in (11) R, - Ar, '2 a ArC12. Accor"
Card i to the scheme mentioned, the authors synthesized compounds of

Some Derivatives of It2#3-Triaminopropans SOY/79-29-2-38/71
the 1#2,3-trlaalnopropan* series which have aryl and aralkyl
radicals at the central nitrogen atou. The a-f-dl*hlorohydrize
of glycerin (111) was condensed with the secondary anine (dl-
methyl anine, diethyl asine, piperidine, morpholine and box&-
methylons lain*)* After treatsent with thionyl chloride the
aaino alcohols (IT) obtained passed Into the maino chlorides (I)t
The last stage of reaction oosprised the condensation of (T)
with secondary asinee of the type btntyl aniline In toluene and
the addition of sodlus aside on hosting. The separation of (11)
was oosplicated (by-processes). Through distillation of the
reaction produote in vae-Au2 It was possible to obtain oospound
(11) in pure state (yield 25%). Due to their hygroscopic ftatur*,
the chlorine hydrates (11) could not be obtained In crystalline
tat* whiah holds also for sulfate* and oxalat*9 for the so**
;
sssan~# For the purpose of aharaoterising the produots (11)
obtained the authore synthesized their Iodine motbylateel lim
thts'prdooss only sonolodin* metLylates In pure state resulted
in all cases. All preparations produced exhibit a very weak
OP&SMO]Ytio activity. There are 3 tables and I reference.
Card 24, 14_44_r~ 0- AMC /S-fO-

501/79-29-2-39/71
AUTHORBs Koahetkovp No I*# Khosatova, To. Do
TITLZ: Investigations In the Series of Isoxasole (Issledovonlys v
ryadu Isoks"ols). VIII, 31sotrophilic Substitution in
Isoxasole (1111, IlaktrofIllnoys, sameshchonlys Y lsokossole)
PIRIODICALs Zhurnal obohaboy khtmill 19599 Vol 29, Xr 29 Pp 535-539 (MR)
ABSTRACTi Many fundamental problems of the ahsalstry of Isonsols, have
hitherto remained Unsolved in *pit* of MMY stu"es an this
nbjoots. The problem of the aromatic nature of this high-
ly'Inter,esting heterocyclic systsa, far Wtanoa, has not
yet boon o2pleloods In oonnectlon heresith, the
the reactions of olootrophillo substitution in the series
of Isoxasole, and their comparison 91th the corresponding
rosatlons of benzene 4~4 the aromatic heterocycles &T0 of*
certain imporund . fbough individual n1tratior4,,svlphtw1-
sationtand halogs:a;1one TR-ofs iv 2p 3) of som* substituted,
INOX4301*8 are known, they more not investigated systsbati-
cally and so far no attention has been devoted to them, at
all as far to isoxazolo is ooncerne4e kooording to previous
nitrationp, brosinatione and morourations of P-phsayl Is*-
Card 1/3 xasolo (Ref 4), in the course of which the substitution took

901/79-29-2-39/71
Investigations In the Berles of Isaxasole. V111. Electrophille SubstituUM
place primarily at the Isoxasals ring, It was necessary he"
to draw respective conclusions as to the relative activity
of lsoxasole compounds In the reactions of slectrophillo sub-
stitution. Thor*fors, the simplest representative of this
alasso lot* loosasole itself).vas subjected to the above-
21*ntionod reactions. It was shown that 1saxasals, in elootro-
pbillo reactions of substitution is considerably less "tive
than benzene and offers only suall yields. On the nitration
of Isaiasd* with a mixture of n1tria and sulphuric sold 0)
the authors obtained the nitro derivative (soltine-Point 47
in a yield of 3.5% only. they determined by experiments that
the nitro group can oaouPy only Position 4 In nitro-isox"als
(Sahose 1). Bronination could be carried out only If isaxatolo
was heated for a while with the equivalent saount of broalas
in the presence of pulvoilsed Iron. The yield of crystalline
bromide (aelting-Point 44 )axiounted to 10. Also in this
a&** the bromine atom Introduced *couples Position 4 (Scheme 2)e
The ou2phurtzation of Inoxasole could be carried out only an
beating with olous within a few hours over the boiling voter
bath (yield of the oulfo said: 174). This Sulfa 8014 was
Card 2/3 identified In the form of Its bbensyl thiourat*: Isoxazols

BOY/79-2,9-2-39/71
Investigations in Abe Urise of Isoxasole. 1111. Bleatrophillo Substitution
in 14clazole
is slallar to pyridine with respect to Its capability of
sloctropbillo substitution* There are 9 references# 3 of
which are Sovlet*
ASSOCIATIONs Moskovskiy gosudaretwo universitat
(Moscow state 'UniversitTy
SUBMITTIM Dooluber 17j 1957
Card 3/3

AUTHORS: KgchetkgjA.L%.J,,* Budovskiyt 8. 1.0 BOY/79-29-2-59/71
Xh6a-u "ot R, X., Karpoyskiyp Us M.
TITLIC: Cycloserine and Related Compounds (Talkloserin I radstionnyYs
soyedlnonlya)s Is Cyclisation of a-B*nsoylamino-P-Arylacryl
Hydroxasto Acids (I. Taiklisatetya a-bonzotlasino-o-arilakril-
gidroksamovykh kixlot)
PERIODICAL: Zhurnal obshchey Wall, 1959, Vol 29, Xr 2, pp 635-642 (USSR)
ABSTRACT: On reacting hydroxamio acids (1) with HC1 and HBr the corre-
sponding hydroxamic acidn (11) could be expected to form,
leading to compounds (111) by the action of alkali lyos. As
is known, however, compounds (1) ntq cyclize In another manner
with hydrochloric said, i.e. under formation of compounds (11)
(Scheme 1), The latter possibility (way B) was carried out
according to reference 2, on the cyclization of a-tonloylgAino-
-0-phanyl and a-benzoylaaino-p-n-mothoxy vh*nylacryl hydroxanic
acid into the corresponding js1ds=1W no (IT), In a 50 and 16 J9
yield. The authors therefore closely Investigated the cyall-
sation of a-bonsoylasino-p-arylacryl hydroxanic saids In order
to determine the influence of the substitu*nt It the aromatic
Card I nucleus upon the direction (A) or (1). On treating those

Cyoloserln* and Related Compounds. V. Cyclixation SOV/79-29-2-59/71
of a-Donsoylamino-P-Axylaoryl By4roxamic Acids
compounds with HCI or ffBr In mothanolp dioxan, acetic sold
and within a wide temperature range (from -50 to +1000) a
slight cyallsation, almost quantitative, was obsorvod# =4*r
formation of imidazollaolone (IV), whereas the formation of
affiliation products of hydrogen halides of the type (Ir) was
in no case observed. Thus It became evident that the reaction
for M# regardless of the character of the substituonts in
the nuclousp proceeds In the direction (B). The ayntbosle was
worked out of-2-pbenyl-5-arylldone ialdazollnt- All 2 -ol.3-
-one-4 (IV) by the cyclisatlon of P-aryl-a-b*nzay2amlno, aaryl
hydroxamic &aid with hydrogen halide In alcoholic or acetic
sold solution (;3 % to quantitative yields). The compounds ob-
tain*d develop a high bacterial activity, In which connection
the substitution of the X-hydroxyl group In then by the moth-
oxy group or the hydrogen atou causes the activity to disappear
Thor@ are 3 figures, I table, and 10 reforenceog 2 of which
are Soviet.
Card 2/j--

FVqTjo&sP-&AoqW OR& 0XITATIon BIT
adols 110joldwoo outiesoloto j0 duois OUTRU sqt UT COTID111eqns
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:8800LAV

Cyoloserine and Related Compounds. It. Synthesis of 301/79-29-2-60/71
Cycloserine Analogues With-& Substituted Amino Group
cyallsation of the I-substituted substances of P-ohloro alanine
hydroxamlo soide Into the derivatives of 4-aminalloolasoll-
done-3 to preferable to the other schemes suggested by the othw
authors. There are 3 references, 2 of which are Soviet.
ASSOCIATION: Institut far"kologit I khisloterapii Akad*ail **41tainskikh
nauk 8881 (Institute of Pharmacology ane Chemotherapy of the
Academy of Medical Soleness, USSR)
SUBMITTZD: December 17, 1957
Card 3/3

AMORS: Xoob*tkov, No K. Kudryashov# L. I., BOT/79-29-2-61/71
-Sonchenkova#
TITLE: Reaction of O-Cblorovinyl Ketones With P-DIcarbonyl Compounds
(Yzaimcdaystviye P-M"vInI1k*tonov a P-dikorboallInyal soy*-
dinentyani). VIII. Synthesis of Polyoubstitut*d Benzene Dortv&-
tiToo. A low Reaction Type of Dien* Synthesis (VIII. Sintes
polizameshchenUfth proisvodnykh b&nzola. lovyy tip reaktoll
diyonovogo sintesa)
PIRIODICAL: Zhurnal obshchoy khIml,ig 1959, Val 29, Nr 2# pp 650-657 (USSRj
IBSTRACT: An earlier report (Ref 1) described tht reaction of 0-chloro-
vinyl ketones with acetoacetic eater In the presence of potash
and It was shown that this reaction does not have a well-
defined character. Ethyl ester of 4-alkyl sallaylic said forms
as chief product when there to a groat excess of acotoacetic
ester. With a lower excess of aootoacetic ester also the y1*14
In 4-alkyl sallaylate drops abruptly, so that In the case of
the reaction of'asthyl-p-ohlorovinyl ketone with acotosootto
eater It Is made possible to Isolate In large quantities a
crystalline product with the melting point 00. The prevent
Card 1 paper deals with the explanation of the structure of this

Reaction of p-Chlorovlnyl Ketones Witb P-Dicarbonyl SOY/79-29-2-0/7i
Compounds. Vill. Synthesis of Polysubstitutod Benzene Derivatives. A low Re-
action Type of Dions, Synthesis
product and Its analgrase, as well *a Its way of formation.
Uperisonts gave the following results: On condensing 2 mole
of nothyl-p-ohlorovinyl ketone with I sol of aa*toao*tic aster
in the presents of potash, the ethyl aster of 2-sothYl-3,541-
acetyl bonsoia &61d to formed. A #chose is suggested for the
formation of this compound, according to which in the first
stage the product of monoketovinylation In its onol &hap* *uttts
the reaction with the second molecule of P-chlarovinyl ketone
(diono synthesis). Thus it In established for the first time
that the unsaturated dicarbonyl compounds are capable of play-
Ing the role of dienoo In the reactions of dione synthesis.
Like various 0-chlorovinylkotones, also P-d1ketones ore, capable
of this reaotion9which has a general preparativ* significance.
It in also important for the synthesis of various polysuUsti-
Wed benzene derivatives. On the basis of the structural
experiments, the product sith the melting point 610 was found
to be a benzene derivative# showing an acetyl, carbothoxy and
methyl group in positions 1,2,3 and 5. There are 10 references,
Card 2/:~ 6 of which are Soviet.
rx*Ot~ - -- 1~ -

Nuaheror&, is rep Imomu,,.vv, R. X.0 SOT/79-29-3-34/61
BUdovlkiyt Is lot Tovdakovp To ?a# Koobetkoyt It I#
TITM Synthesis of the Thiosaide of the 2-tthylisordootinia Acid
(Sintes ticaulds, 2-otilitonikotinovoy kleloty)
PERIODICALs Zburnal obehohey kbiall.,1959# Vol 29, Or 3. pp 915-919 (USSR)
ABSTUCTs Recently the high chowtherapoutio activity of the thioanidal
of some heterocyclic a.aide was reported# In particular of the
thicamids, of the 2-othyllsonlootinic sold (Rot 1). This
thioudde, exceeds by its efficacy many other tuberculostatioa
against sycobacterium tuberculosis,, The synthesis of the
thioasids.of 2.sthyllson.~cotlulo sold described In publications
(Rot 2) 10 too complicated (of sevoral steps) and not suitable
for a large-scale production. In the present paper a simplor
synthesis of this thloamids, according to the given scheme to
descritedo The Initial ethyl pyridine (I) synth*sisod according
to reference 3 was oxidised with peracotio aoid to eive the
X-oxide (11) which was trwuformod by nitration into compound
III)* In the reduction of (111) the 2-stiql-4-saimpyri4ina
Card 1/2 IIV)(90% yield) was formed# The bromide (V) was obtained by

Synthesis of the Tblosside of the
2-L'thyllsonlootinto AM
SOT/79-29-5-34/61
treating the pevbrozide~of (IV) with sodium nitrite In
concentrated hydro'brosic said (Ref 4), This reaction proceeded
smoothly and gave a high yield In (T)a For the transformation
of (T) into the sitrile the former was heated with copper
0710ide, The domplex Cospound. Initially formed was decomposed
by ammonle. Into compound (71) (yield 70%). The last st*p.of the
synthesis was the transformation of the nItrIls (VI) Into the
thio"Ide of the 2-othyllsonlootinic soid (VII) which was
obtained In orystalline fore In high yield by the saturation
of the solution (VI) In pyr1dine, with hydrogen disulfids to
the presence of triethylanins, In saltless state it to
slightly. soluble In irat*r. Th4ire are 6 referenc4se I of which
Is Soviets
ABBOCIATIONs Nauahno-iselodovatellekly Institut
-(scientific Research Institute of
Chesotherari)
SUBMITTEDs February, 4# Ms
Card 2/2
faraakologii I khlmlot*rspil
Pharmacology and

5( 3) BOY/79-29-4-60/71
AUTRORSt lochetkovp 1. K.o Gottikh, 3. P., Shtumpf, Rollf
TITLZs Reaction of O-Chlarovinyl Ketones With O-Dicarbonyl Coupounds
(Tialmodeystyly# 0-khlorvIallketonov a A-dikarboallInyst soyedi-
niyasi). 11. Ketovinylation-of the Eaters of Cyclic P-loto
n
A Ids (IX. Ketoviallirovantle ofirov talklichoskikh 0-ketakielot)
:
PZRIODICALt Zhurnal obsbahey Wall, 1959, Vol 29, Nr 4, pp 1320-1323 (0831)
ABSTRACTs In connection with previous investigations carried out 'by the
author* (Refs 1-5) the ketavinylatlon of the *store of oyallo
keto &aids Is discussed In the article mder review, and now
prospects for their synthesis are given. Subject of the oxasina-
tion were the ethyl esters of cyclopontanons- and oycloboxanone
oarboxyllo saids containing active Ildrogen and therefore "pablo
of being easily kotominy2aUd (Hot 6). The ketoyiny2stion of the
said 0-keto esters was carried out by reaction of the sodi=
derivative of the O-koto ester suspended In benzene with
0-ohlorovinyl ketone# accorling to references 2 and 3* The reac-
tion, which met with no difficulties whatever, neither In the
case of alkyl O-chlorovinyl ketone*, nor in the *as* of their
Card 1/), arozatto analogues, resulted In nornal katovinylation products

SOV/79-29-4-60/77
Reaction of ChlorovWl Xotooes With O-Dicarbonyl Compounds. IX. UOT18tyla
tion of the taters of Cyclic P-loto Acids
Card 2hk,
with yields ranging from 60 to 70% (Behan* 1). After the usual
treatment the I-earbothozy-l-(30-kotoalken-11-yl-lf)-ololo-
alkanones-2 wore removed by distillation (a** the experimental
part). In prinaiplop this rotation does not differ fro* the
kotoyinylation of a-alkylaostavotic eaters (Ref 3). In order to
realiso the kotovinylation of other 0-dicarbonyl compounds of
the alloyallo serles, ono of the representatives of cyclic P-di-
ketonest Viso loi#4-trinothyloyclohoxaa*diouo-3t5 (*ethyl-
dinedont) was ketovinylated. After many, partly unsuccessfuls
experiments the conditions war* found under which It to possible
to prepare a kotoylaylation product with an output of between 30
and 350 (Sohoa* 2). When hy4rogenated this product absorbs I mol
of hydrogen# which suggests only on* double bond, and does not
yield a 1#3#5-trizattyl benzene with diluted act4s, which sug-
gests a 0 derivative. Those results confirm the theory of the
structure of the product obtained and prove the fact that It Is
possible to apply ketovinylation to cyclic as well as alicyalla
0-diketonom. Thor* are 6 Soviet references.
or /Ow-s' ('/Sse

A.iHORS:
Kochatkov, 11, Z,j COMM, B. P. SOIr/79-29-4-61/77
T
.t!TLE-. Reaction of the P-Chloraviull Xotonos lith P-Dicarbon$l Cov-
pounds (Tzainodeystvi'79 P-khl orvi,11 Ike tonov a ;-dikarbonillr4al
soyodinenlyami)s 1; vf the a-Pyrone Derivatives Froz
a-(3-Ketoalker4l-l~=ds (I.roi-jot.qni Lzr,)dnykh
.39 pro
a-pirona iz a-(3-ketoaIkenJl-1)-P-k9tok1i
PERIODICAL: Zhurnal obshchej khimli, 1959, Vol 29, Itr 4, PP 1324 - 1)2e
(USSR)
ABSTRACTs This is a continuation of previous InvestiCatioAs (Refs I-A
The authors tried In the pras~nt papor t~) Md the conditicts
for the alkali ketone oleavago of the a-aIk;rI-a-(3-kGto&lk*nyl-
-1)-acetio &old *star wh4.ohg hovey9r, failed, low they trial to
carry out this ketone cleavage b,, &-% acid method and failed
again, although the reaction vieldod a certuain result 1. a.-3t6-
Card 1/3

Reaction of the P-Chlorovinyl Ketones With P-Dlcarbon;(l .307/700-29-4-61/77-
Coppounds. X' Pr"antice of tho a-Pyrono Dorlyatlyos Fro2
a-(3-Xetoalk9nyl-i)-P-X9to Acids.
R
I Heloca 3COOH
CH3Coe CO2C215
CH-Cacolto
as 0 O'VO R-C 2~51
H'ftCH51C2H5PC3Hj#
This reaction Is carried ont beat In tho ~!ase of heating of the
ketovinylized ester of 0-koto acld with a mixture of hydro-
chloric-.and aoetio &old# The structure of the reaction pro-
ducts was proved by two different cathod& (Aazord.lne to ee!-~*zo
2 and by Its hydrogenation)e Thus an sold cleavage takas plate
In this reaction# accompanied by a cyclization of the produca4
ester of the unsaturated 6-k*to &old Into the a-p7rons deri-
vative, In this ease the ptesence of the katorinyl grour In-
fluenoss the reaction direotlon considerably@ This to soi well
the case with the acyl group.,Schoae 3 d4constrates tb* OxAnPle
Card 2/3 of a normal reaction of thit ketone 4otosposition, In the ago* of

Reaction of the P-Chlarovinyl Utones With P-Dicarbonyl 30'F/79-29-4-61/77
Compounds. 1) ft"exatUnof the a-Pyrone Derivatives Yrom
a-(3-1rQtoalk4ny,L-1)-P-xGto Acids
the absence of the ketoalkenyl group. The provailinC &aid de-
composition of the enter of the a-katoalkenyl-o-keto acids and
the subsequent cyollsation were furthermore used for the sTr;-
thesis of the h itherto unknown o.&(a-pyronoyl)_carb,oxyl1o acids
(Scheme 4)* Thus the resulta of this Investigation show that
the transformation of the products of ketovinylization of the
asters of P-keto said* Is under the Influ*nco of acids assumed
to be a general synthesis of various a-pyron* derivatives which
for their art serve of &.source for Ithe synthosts of oth*r
compounds fast 27T- There art' 7 Sevi*t references.
ASSOCIATION: Institut farsakologli I khInioterapti Akedecii meditainakikh
nauk 888R (Institute of Fharsaooloiiy and Chezotherapautics of
the Academy of Medical Sciences, TJ33R)
SVMTTM): March 6, 1958
Card 3/3

AUTBORS: OT/79-29-4-62/77
Khanutoy, 2, X,j rArpolskly, M. Yost
Budovskly, 1, 1.9.9overin# Yes Sol
TITLS: Cyoloserine and Related Compo-wds (Talkloserin I rodstvonnyye
CyolotreoninO [!II.Slntes 5-OWI-4-asinoisoksasolidona-3
tsiklotreoninall
~
PIRIODICAL: Zhurnal obsbahey khIsill 1959, Vol 29, Ir 4, pp 1328 - 1333
(USSR)
ABSTLACT: 14 the present paper the sTuthesig of the
asolidone-3 (cyalotroonins) is desorib*d. The reason for this
choice was the authors' desire to use the method earlier torktd
out by them (Rafe 1#2) for the synthesis of the 5-substitut#4
homologuts of ojoloserize# and *inns the latter Is genetically
related to the vital amino sold-treonino. This fact permits the
assumption that ajolotrsonta6 is to sell biologically active.
When this Investigation was fInIshed a report gas published
(Noft 4,5) on the synthesis of cyclotroonine from tr#onine *ter
Card 1/3 the corresponding hydroxamic ncid. The synthesis of OyclotrW&J-ns
(VI) carried out by the authors Is Illustrated by sob*** Is, The

Cyoloserine and Related Compounds. BOV/79-29-4-62/77
VII Synthesis of 5-gothYl-4-Aninoisoxasolidons-3 (Cyolotroonine)
initial product (1) was obtain:d b- +he chlorination of *ethyl
crotonsts In methanol at 10-15 OB-60% yield)# contrary to Vie
con licat d presoriptions in the publications. The condensation
of 11) wNh the sodium derivative of acetoxime (Rof 2) led to
the aster (II) which was S&;onified Into the acid (111). Cos-
pound (111) yielded the amino &aid (IT) (5V,.) withemse lIquSA
ammonia at 45-500 within 8-10 hovre. The hydrogenation reaction
CH
3>0 -1-0- was used for the determination of their stracturet
3
since It proceeds without contact with the asynnetrical P-o arbon
atom (Scheme 2)* This may it a now method for the determination
of the struature of the-a-&Mno-o-isopropylidtnaaftoory aoldss
The result of the reaction was tho s&;&r&tion (87%) and the
Identification of the dsi-allotreoning which points out that(IT)
belong# to the erythro series# The next stage was the trazaltion
of the amino &aid (IT) to the conpound (7) (50-60%). The last
stage consisted In the oyolization of the dichloro hydrate (T)
Card 2/3 Into the oyolotroonine (TI) by a oa~jstlc ;otash solution In

Cycloserine and Related Compounds* SOT/79-29-4-62/77
VII Synthesis of 5-liethYl-4-Aminolsoxasolidons-3 (CIrolotroonloo)
methanol solution (00-85%). Since 'he atz-actur la not chaiced
by the cyclization the formula Qi;-~P
lidone-3 *an be ascribed to the cyclotroonins. The atruct-i" in
also confirmed by the data of the Infrared s;ectrum. Its slail-
arit)p was determined by means of the pa;er chrosatoiraphy.
Cyclotroonine has a distinctly markel antituberoular actiTit7.
There its i figure and 5 rottrencesp 3 of vh1ch are Soviet.
SUBMITTED: Yebruary 10, 1958
Card 3/3

AS4029: Khoamtovat TO& Do# 301/79-29-5-WT5

TITLE: synthesis of 6-Aryl-licatine Aoids and 6-Aryl Pyridines
(Sintes 6-arilalkotlnovykh k1slot I 6-arilpirldisov)
PnIODICAL: 2hurnal obahchey khlail# 19590 Tol 29, Ir 5g pp 1651-1659

ABSTRACTs Earlier pepe'ra (left 1-4) doearlbod the use of pookloravlayl
ketones and their derivatives far the synthesis of derivatives
of ulootinto sold and pyridlao. 4 using aryl-0-ahlorovWX
ketones the earrespondlag MI-substituted derivatives a"
obtafted* The synthesis mar be carried out by condensation
of aryl-o-ablorovinyl ketones with sastoseetle ester and
&maul& or with aninoorotoolo sold ester, In both asses#
phenyl-$-chlorovinyl k0ton* or Its derivatives (9-ohloro-s
"bloro-# p-mitrophonyl-p-oblorovinyl ketone) yield after
several hours of tolling In benzene the corresponding eater
of 2-methyl-6-aryl-nlootinlo said In a yield of from
dry-distillod with
50 to*65 %. The saponified @star* wor*
_
soda Has and gave the aarrespanding 2 sethrl-6-aryl pyridines.
Card 1/2 The experimental ... describes the aourse of the syntheses

SYSthesis of 6-Aryl-glaotinle Aelde and 6-Aryl Pyridinos SOy/19-29-5-53/75
and gives the analytical and physical data of the compounds
attained. there a" 9'reftrenceag 6 of which are Soviet.
ASSOCIATIONt Moskovskly #*svA&rstv*nn" univeraltot (Noscow Mte Valvorstir)
SUMTTZD: lpril 14# 195S
Card 2/2

15WORS! Kodhetkovj 1* 1,,# DuOkinao IL V* BOT/79-29-5-54/75
TIM: Aalnoaoyl- and Aminoalkyl Derivatives of Box* Aliphatic-
troattle Amines ("InoafallOnyyo I "Inoalkillnyyo
prolsvokWe askotorykb shiracarosatiabeekikh aminov)
PnIODICALs Zhurnal, obehohey kbiallp 1959, Vol 29, Ir 5, pp 1659-1664
ABSTRACT: In previous works (Refs 1-3) obloroaryl derivatives of
aliphatic-aromatic aulnes were described, some of which
proved to be efficacious spassolytics, In the course of the
further research made to find agents Influencing the central
nervous systeaq the authors carried out the syntheses mentioned
In the title and the Iodine alkylates of the compounds
obtained war* prepared. the derivatives invostigatod possess
the general composition: 11INCO(eff 2)nS(C2N5)2 or
R1R(CN2)AX(C215)2 In which 'coanection 2 Is equal to C63 5CK2#
C05CYN20 005C12CE06150 C61 5CICIC6a, or C6R,CRC1C69,#
Card 1/3 Oil OCR3

AnInoaoyl- and Aminoalkyl Derivatives of Bono 301/79-29-5-54/75
Aliphatic-Aromatic Anines
Aoylatlon takes place under the effect of halogen-
substituted acid chloride upon the &*Ins In the presence of
alkali in an emulsion of water and ethyl ststate (or
fte chloroacyl auldes obtained wore treated In boiling
toluene with an excess of disthylasine and the d1othylamino-
acyl derivatives wore produced. With Iodine ethyl they Save
the iodine olkylatest which resulted as oils but which could
be crystallized after a corresponding treatment# In order to
compare the physiological efficiency also ths corresponding
dialkyl amino compounds were synthesized according to the
well-known method (20f 4). to prepare the diothyl amino prop!yl
derivatives the authorsapplied for the first time the
reduction of diotbyl amino proplonavido with lithlun alminva
hydride. this convenient mothodt seouring a high yield, say Us
very useful particularly for the synthesis of derivatives with
long alkyl chains. ?be preparation of Iodine othylates Savo
only quaternary monosalto with all derivatives obtained. This
phanomenon.has not boon clarified as yet and requires more de-
tailed Investigations. The compounds synthesized were chocked
Card 2/3 in the pharmacological department of X. T, Kaverina.

Aninoacyl- and Aalsoalkyl Derivatives of Some BOY/79-29-5-54/75
Aliphatic-Aroaatto Amines
All P-ohloropropionle &aides showed no spassolytic effect,
Son$ coapouds oven Increased the motor activityo
p-dialk,11-asizoalkyl &aides did not show any analgetic
effect Their quaternary malts exhibit a certain bypotonalvat
spasaoiytio and ganglia-blooking effect. fte *xperlsontal
part jiv** the data for the synthesis of the compounds
descrilbod. Table I gives analytical and physical data of the
I-substitute& P-ohloroproplanic "Idess table 2 the** the saw
for the I-substituted distbyl &also proplonaal4es and their
Iodine sthylateso table 3 the same for the I.sutstlttted
11#11-diothyl-otby2eno dlaalues and their Iodine ethylaUs.
there are 3 tables, and 9 references# 3 of which are Soviet.
ANOCIATIONs lauahno-Isslodovatellskly Institut faraakologil I kbinoterapil
Akadonti seditelaskikh nauk 9851 (Solentiflo Research Institute
of Emmoology and Chemotherapy of the Aoadeor of Medical
soleness of the 0381)
SVMTTXD: April 14# 1950
Card 3/3

ADTHORS: xo*h*tkovA-Aj Ifantlyort Z. T*.1 501/79-29-7-0/83

TITLZ: Synthesis of the I-Aoyl-2~chlorocyolopenten*-1 and Sthylono
Ketals of 2-Acylayolopentanones (Sintos I-atell-2-khlortolklo-
pontonov-11 e11I*nk*%&l*y 2-atmiltolklopentanonov)
PBRIODICAL: Zhurnal obehohoy khWIq 1959, Vol 29# Nr 7, pp 2324 - 2329
(USSR)
IBSTUC28 Up to tho present date only open chain derivatives of the is-
ortant P-ablorovinylketones have been Investigated in attall

Rofs 1t2#3#4t5),, Alloyolic representatives of this *I&** have
~
practically boon unkzown up to the present. Two contradictory
reports have boon given concerning the synthesis of I-acyl-2-
chlorocyolohozon*s by the condensation of cyclobessnono with
acotyl chloride in the presence of LlCl, (Refs 6,7)s In *xton-
$ion of a previous thorough Investigation (Rof 8) of-WAs r*-
actiong which up to date presents the only possible way of s;rn-
thesising the hitherto unknown compounds of the afor*-sentioied
type# the authors carried out further extensive studies. The
Cara 1/~ reaction of oyclopentanans with aeld halides In the presence of

S;tnthesis of the and 3OV/19-29-7-48/83
,Sthylone, Ketale of 2-Aayloyalopentanon*9
AM 3 was of a general nature and yielded the b1thorto unknown
COB
+ RCOCI AlCl, t
ICI *her* 1.42300285t
C3 879iso-c 499.
The roaotion proceeded most favorably when oyolopontanon# was
added to a previously prepared mixture of tho &aid chloride and
AICI In dichloro ethane. the roxotton mechanism to given in
3
$*home 2, The I-s.eyl-2-ahloroololopentenes obtained were rather
Instable oily liquids. Bssid*s tpectroscopla data the ozonlas-
Uon of I-aastyl-2-ohlorocyclo entene-t was decisive for the
verifloatIon of the structure f8ahose 3). Thus, the experiment-
K1 results showed that in the cyclopentanon* series the above
reaction yields alp-unsaturated ketones, oyolia wtaloes of
Card 2/3 ft-ohloroviarlkstonel whereas In the cyclohexanone series the

Nathosis of the I-A0Yl-2-ch1orooyclop~nt~n*.t and SOT/79-29-7-48/83
Ithyleno Notals of 2-Acyloyolopentenones
same reaction gives Pt unsaturated ketones as main products.
It was shown that the (a-logsn in I-acyl-2-chlorocyclopentenen-1
is less mobils, than in 0-ablorovinyl ketones# By the reaction
of the above pentenos-1 with ethylene glycol in the presence of
ION the hitherto unknown ethylene kotals of 2-acyloyalop*nta-
nones were prepared* there or* 19 references, 16 of which arn
Soviet,
ASSOCIATION: Hookovsklygosudarstvow4y universitet (Noscow State Univers.".1y)
SUMMED June 5, 1958
Card 3/3

5(3) S 2 9 - I
AUTHORSt E, Ye., N(1104tsov# N* To
TITLEs Brominatlon of P-Te%oac8tA1s(DromIrvv&niy* P-ketoatsotalty)
PWODICALt Zhurnal obehahey Wall, 19419, Tol 29, Or 7, rr 2330-2337 11CUR
ABSTRAM Hitherto the easily actessitle 0-ketwetals RCOC92CII(cut) 2
were used either as potential Vdicartot4l ccmpoun4a (hofty lg4)g
seeing they resemble the P-nbloro-il ny1ito tones In their renctions
or as ketones having another r*aotiva substituent. A third
possibility# Its* that of introduoing substituents Into the
zentral nothylene, group of the ketoacatal, has so far been
disregardedg even though the resulting con;0unds could be
utilized for synthesis In various directions (R*f G), " firat
reaction of this kind the hitbArto unknown broaination of "Who
ketoa2etals was undertaken. Thusp two methods were elatorau4,
one for the synthesis of cx-broiao- ft-ketoaldatqdea by bror;nxtin
of P-katoaldshydoa In aqutous solution In the prosenco of
barium carbonate$ and another for tho preparation of ethylene
acetals of cK -bromo- P -ketoaldehydas by treaination of thit
ethylene acets,19 of 0-k-7toaldphydos In other In the presence
Card 1/2 of barium carbonate By ronlonuatir-ti a, -tropo- P -ketoaldehydes
0 cc

Brominatlon of P-retoa-aftals
SOY179-29-7-4918.'
with urea# the 2-amino-5-acyloxazolva were ottained; on
condensing with thiourea and thioasides of acida 2-substit-ated
5-soylthlazolee me" formed. Thus# it was desionstrated#that the
cc-bromo-ft-ketoaldehyd*9 reaot similarly to a-bromoaldehydes
-in the reactions under InvestIgatton . On treating othylone
-soetale of of-briono-p-ketoaldehyden with P-naphthol In the
presenae, of iron chloride and hydrochlorio acid 2-41kyl-3-broso.
naphtho-(1#2j5#06%):pMl salts were tomed. Table I shows tho
synthesis of the of, 'broso-A-ketoald*hydess
~0
I-CW.92r. C and table 2 the synthesis of the ethylono
aostals of at-bromo- ketoaldehydest
1-110 - P2
a - 00 - CHDr - CH I a
NI-10 -CH2
There are 2 tables and 15 referomios, 6 of which Are SOT1"t,
ASSOCIATIONs Moskovskiy gosudarstvannyy %iniversitot (Uosc,,)* State Univqrsity)
SUBUITTEDs June 5# 1958
Card 2/2

50)
AMORS: Kochetkov, 1. lag lifantlyovg 1. Yoe# Sokolov, 3, D.
TITLE: Synthesis of Aromatic P-lotoaootals
PERIODICAIi Zhurnal obehohey khIsti, 1959, Vol 29, Wr So pp 2570-2575
(USSR)
ABSTRAM The 0-ketosoetals which are sainlz obtained from the correspond-
ing P-ohloro-vinyl ketones (got i) are r*cently of aanifold
use in or#&Mo synthesis# whereas compounds of this class with
aromatic radicals have nearly escaped notice (Refs 2-5). quit*
recently#--tho authors synthesived the ethylene &*4t&l of the
bonsoyl-aootaldehydo (Itof 6)o Presently, they carried out the
synthesis of various aryl-0-ketoaostals using, as initial
produats, the "yl-P-ohloro-vinyl ketones which are now well
accessible (Id 7). thres now representatives of this OlAost
.the o-tolyl- and notolyl-P-ohloro-vinyl ketone$ and the A-
bromo-phenyl-p-obloro-vinyl ketone, were synthesized. On the
first attempts to obtain the acetal of bonsoyl-&cotaldohyde
&000rdiUC to reference 1# the PhOAyl-P-MOtbQ1y-Tinyl ketone (11)
was formed instead of the expected compound. ThIs was do* to
Card 1/3 the catalytic action of alkali traces loft over In the re-

SOY/79-29-8-24/81
Synthesis of Aroeatio O-Kotoacetals
action,, Therefore# the reaction conditions were altered in
such a way that In the distillation any traces of alkali were
excluded by treating the reaction alitur* with water, W ox-
traoting with other. Thus the aostal of the bonsoyl-scot-
aldehyde (111) resulted in a 60% y1oldo Nors, convenient a"
the ethylene sootals of the 0-ketoaldshydes which were recently
mynthealsed by the authors (Rof 6), Prom among the repressotao
tives of the aromatic sort**# only the ethyl*no acotal of the
bonsoyl-aaetaldshyde (IV) is described in publications. The
fact that the cyclic ethylene aootals, which can easily be
obtained by rtection of 0-ohloro-vinyl ketones with ethylene
glyool#-aro formed by treating both the disethyl aootals and
the alkoxyqvinyl ketones -ith ethylene glycol in the presence
of alkali, Indicates their considerably higher stability, All
transformations dosoribodp which are connected with the In-
vestigation of the stability of the &**tale of the bonacyl-
acetaldshydet are Illustrated in *chose 1. 109 and 121003
(Ref 6) proved to be the agents most useful for condoneirg the
ethylene acetals of the 0-ketoaldehydes of the aliphatic
seri*so The operational method devised for the synthesis of the
Card 2/3 first member of the series was further applied to the oya-

3ynthesis of Aromatic P-Kotoaoetals SOV/79-29-8-24/81
thesis of the ethylene acetals of the 0-ketoaldshydes substi-
tuted In the aromatic nucleus, using 102 and 1 2Co5AS con-
densing agents (60-W% yield):
Ar0O_C&CHC1 JoArOO-M C
O-CH2
where Ar dm n#moo-CY61351 ago-CIC614 ; n-BrC 614 1 R.CK5 0-C68 4#
The reaultent crystalline scatals are stable, in general well
soluble# and do not color with ferric chlorides There are
I table and U references, 6 of which an Soviet.
ASSOCIATION: Moskovskiy gosudarstyennyy universitst (Moscow state University)
SUNITTEDs July 3t 1958
Card 3/3

3 (3)
_
AUTHORS: 41ghatkovt No top Ambrush# Ivanq 001/79-29-8-26/81

TITLZ: Aoyl-pyrasoles, It. Bynthesis and Constants of Acidity of
3-Arayl-pyrasoloo
PERIODICAL: Zhurnal, obahchey khiali, 1959p Vol 29, Ir S. pp 2578 - 2583
(Uses)
ABSTRACT: Previously (Ref 1) the authors presented data concerning the
acidity properties of gone 3-aayl-pyratoloag &ad tried to
interpret the nature of Use 0
roperties. In contrast with
the earlier conceptions (lef and A. No Nesseyanov and
,5
go to lochatkov (Ref 2), they concluded (R*f s) from the in-
frared spectra of the 3-aeyl-pyrasolos and their salts that
the salt forsation, is not due to a tautonerias of the bon&*
in the system of the $-acyl-pyrazole, but to the occurrence
of the acidity properties of the hydrogen of the ring (3dume 1).
The previously used spectrophotonstric method of determining
the acidity constants of the 3-acyl-pyrasol*o permitted the.
quantitative deternination of the acidity$ In dependence on
the nature of the soyl ra4loal. The acidity of the pyrasol*
Card 113 derivatives and of the nilrog*n-oontaining heterocycles In

Aoyl-pyrasoles# 11# Binthesis and Constants of Acidity SOT/79-29-8-26/81
of 3-AroYl-pyrasoles
general has so far not been investigated quantitatively. Ths,
present paper gives the acidity constants of (1)# with sub-
stituents In the nucleus# which perait the influence ex#rtod
by the character of the o&rbonyl group of the 3-aoyl-pyra-
solono upon the acidity properties of the latter to be judged.
The analogs of the known 3-bonsoyl-pyratole (Rofs 2.4) were
synthesized which have a mothyl-methozy- or nitro-group and a
chlorine atom in pars.-position of the ph*nyl nucleus. The
synthesis was easily carried out according to the aches*
ArCOOR-CICI + CH212 -4 Arco - I - C
I CH M
where Ar a-CH 3P6H 41 S17CH30C684# A-CIC684# a-oeyV
The yields of 3-aroyl-pyvazoles were 40-80%. The constants of
the acidity dissociation were dot*rain*d froa the ultraviolet
Card 2/3 absorption spectra of the 3-aroyl-pyrazol*s, at different

-Acyl-pyrasoles, no'Synthesis and constants Of Acidity SOY/79-29.0-26/81
of 3-Aroyl-pyravoles
percentagecontents of the a*dIum. It to shown that the acidity
of the 3-aroyl-pyrasol9e.depends on the substituent In the
phenyl nucleus# and dsolrsass~ according to the following grada-
tion sahtne: XO 2>Cl>R~C'3 CH30. This to In couplets &a-
oordanoe with the Influence of the s"s substituonts upon the
dissociation constant of the corresponding Wa-substitutod
bensoic &old** The results of the spectrum analysis are given
In 7 diagramise There are 7 figures, 2 tablet, and 12 references,
7 of which are Soviet.
ASSOCWTONs Moskovskly gosudarstvannyy univ*raltot (Moscow State University)
SUBMITTED: July 3P 1950
Card 3/3

5M SOY/79-29-9-1/76
AUTHORSt Semenov Shenyakin, M. U., KochEtkov, 1. 1.
TITLLi Academician Ileksandr Nikolayevich Kesmeyanov,(On His 60th
Birthday)
PLRIODICAL# Zhurnal obahchey khiaiio 19590 Vol 290 Sr 9,
pp 2811 - 2816 (MR)
ABSTRACTs A. N. Xestaeyanov (born 9 .9.1899 it Roscoe) grad~asted from
the Physical and Uathematical Dcpart-cert of Moscow Univc-rolty
An 1922p became an assistant to tho well-knotn chealst 1, L.
Zelinskiyo and later was appointed professor in ordinary
and head of the Chair of Organic Chemistryl he attained the
highest degree In 19471 when he was elected rector. go became
a member of the Academy of Sci#ncte in 1943, and of other
institutions later on. An outstanding speakorp he has a special
talent of rundoring tho most complicated subjects intelligible
and pleasant* His activities have covered various fields, from
a great number of problems belonging to elemental-organic che-
mistry to the synthesis of valuable new polymers# from theore-
tical probless of reaction zechanism and reactivity tc the
Card 1/3 introduction of methods of synthesis relating to the compound

Acadeaiaien Alsksandr likolayevich Nesaoyanov. SQIV/79-29-9-1/76
(On His 60th Birthday)
heterocyclic systems. A-long his numeroas achievertnts
the following deserve first mentions the slaplo
method of synthesizing metal-organic cozpounds by the aid
of aromatic dissocompounds, a method which in still
regarded as the beat :or the synthesis of aro:Latic deri-
vatives of meroQry, antimoNf, arsenic. This method has been
developed to apply to 4;ynthoises of aromatic cozpourdo of tint
zinop thalliumg slumlniW as well an orStnomercury-silver
compounds from compounds of Sn, kb, As, Sb, Cd, T19 and
others. Re=nrkable synthese.,o are the ones yielding Lodonl4a-.,bro-
and chloroniam coapoundst and finally, oxonium
compounds by the arylAtion Df bromo- and chlirobenzene, and
of diphonyl other 'with diazonium borofluoride. Great Importance
has bo&n and still Is attached to his inventigatiom corcerning
the addition of metals to the uneatirated compounds of th#
olefin and acetylene series, the exchange of metal atoms It
the compounds of the above metals cont a ining a fivchl6rovinyl
radicala Meameyanov has developed a new conception of the
manifold'reactivity and displacement of the reaction center
Card 2/3 In the reactions of metal compounds. His attezpt of solving

Academician Aleksandr Nikclayevich Nosmeynnov. SOV/79-29-9-1/76
(On His 60th Birthday)
the problem of the mechanism of electrophilic substitution
an the saturated carbon atom deserves special atntion* He
investigated the metallocenen, =otal-organic compounds formed
by the interaction of the 9,pqd-eloctrons of the transition
metals with the %-electrons of the unsaturated carbon bonds.
The aromatic nature of ferrooone was proven by taxtrous re-
actions, From 1938 to 1954t Ifeameyanov was th4lboad of the
Institut organicheskoy khimi! AN SSSR (Institute of Organic
Chemistry AS USSR)# from 1954 head of the Institut ol*monto-
organiohookikh soyadinsaiy All SSSR (Institute of Elemental-
organic Compounds AS VSSR)1 1946-48, secretary of the Ot-
delenlye khimioheskikh nauk AN SSSR (Department of Cheziasl
Sciences AS USSR), and since 1951 he is the President of the
Akademiya nauk SSSR (Academy of Sciences, USSR)- Since 1947
he is the chairman of the cotuittes presiding over the soientl-
fic Lenin Prize, awards (forzi!rly called Stalin Prize). He was,
distinguished with the Lenin Order, the Order of the Rod
Workers$ Bsn~nert and the St&:3n Prize First Class for Mojent4_
tic aerites
Card 3/3