SCIENTIFIC ABSTRACT MIKHLINA, YE. YE. - MIKHNEV, K.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R001134120017-1
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: June 14, 2000
• Sequence Number: 17
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

Synthesis of 6, 7 -Dl -substituted 1 -A zabicyc I o- 79-28-5-8/69
-(3,2,1)-Octane
ASSOCIATIONs Vsesoy-uznyy nauchno-isaledovatellakiy khimiko-farmateev-
ticheakiy institut imeni S. Ordzhonikidze (All-Union
Scientific Chemical and Pharmaceutical Research Insti-
tute imeni S. Ordzhonikidze)
SUBMITTEDt May 25. 1957
Card 3/3

Hi;-Jtj'.'aya' Ye. S., S
cv, L. Fur Fht i t ~v a, T* "a .
TITLE Syn t.-ir, z-, I s o 'L t:-~e H,-,- z i n e s and Hyd r-i z o..e s -, f So-:.- H- t r- -
i c --r,.d Aro:7~at -' c A- o Sintezz ~7idraz. 'cv i Iraz(:,:.cv
ric~kotorykh t'
PEP, ~iL r- al O~S-C:.ey ~'r i- i i Yol 2~

ABSTRACT In ea ri ~r i.-.v,?s t i at i or. s Re f 1 t w -1 a -It
t e riz 4 ~~e of i.=,i ~-- t ini -ic 1 1 3
dev, 1 o k. in n.-A i t i~ - r-u I - r ic v i t vi ~i t r-l' ,; '-, ,
of interest to t~.e r s t o "3 In t i :~'- t -e Z 6
and r deriv - t ~ ves of t.,.e pyri dy I-4-ace t : c a
~-(pyridyl-4,'a~rylic ind ~ - ( py r i ~', i c, - 4 , - j, r: ,!-i I-i
an t.,.e :;e .1 4 ff Pr f ro-, t:.e i.,~onicotlno-tl
pre~'('-rwe of one '~' (I more t-Tr.)U, 9
p'-,-rili.,,.e nilc.(?,:.,] -d t_- ~.'/ ! r . ~- in , ~ r T
e:; I - 7- fl to 4 r. r -' z 1 , e 7,
frj7, ~ci -,f t~ r i e 11. -1 -,--1 i n ~i r ~3
i n o. ? o e;~ r t:.(2 C * t''-t ;f t...'
on, t i r) t

if Hj
Y r: !:I -'I c
iv r i di 1 u i, i
:.L, Cal 1
u
t a t I irt V; *~Y
o f r,- z
s, -.y ~t z3 - -t r r i e do,l t a o e
e t ~-.-f 1es t r s r) f t j, I r1 -iv i t h r- z
20, ;*,i 0.'.
-t~.

S~;,. t 0 f t. e I--. z c e
r u 13 S') v
A 3 3 AT I N V,,)(-.Ioyllznyy v I y
tic -.eskiy in -,:t : tu t i-!(,ji i S rdz h. on i,: idze (A:'-'
Sc ier t if ic ace - t Re ~-P- a e
S. 31-3Z -.Onikidze
Se.te--i,(-r 23,

AUTHOR5 Purcht at ova, 7 - 'Iir-.hlin a, "e. !e. , 3 -V/'-n-
Rubtnov, V.
TITLE; InvestiCation of the Formation Reacti-,n of 'N-Su~stituted
2-Aminomethyl-3-Vinyl ~uinuciidines (Izucheniye reaktsii
obrazovaniya ~1-zamcshchennykh 2-aninometil-3-vinilkhinukl-
!inov)
PERIODICAL: Zhurnal obshchey khimii, 195~, Vol 21,,, Nr 2, pi, 1177-191) (T_ISS'~'',
ABSTRACT: The question is raised in the present paper, whether the
11-substituted compounda of 2-aminomethy1-3-(0-oxyethyl'j-
quinuclidine can be transformed Into N-substituted comi,ounds
of 2-aminomethyl-,~-vinyl quinuclidine by distilling- the re-
spective stearates and benzoates at normal pressure- Esters
were obtained by t~ie reaction of chlor)c ;inhydridp of stearic
anj benzoic acid with the N-sub,,-tituted com~,ounds of
2-aminomethjl--3-(~-oxyethyl)-,~uinuclidir,e 1.n berizene :3olution
On distillint~ quinuclidine (1~ two quinuclidines (II %n! 1',' '
were formed. They were separated by treating the mixture with
mercury acetate in acetic acid solution, involvin- the sub-
oequent separation of the product of the affiliation -)f
Card 1,'2 mercury ricetate to the unsaturated com.-ound (11) and the

Investigation of the Fornation Reaction of SCV
11-Substituted 2-Aminomethyl-3-Vinyl 'Uinuclidines
separation of (II). Besides (II) and (III) also ethyl 3tearate
was separated. The formation of compound (11) in evidently
accompanied by a separation of stearic acid (Scheme 1). Only
the tricyclic derivative (III) an,1 ethyl benzoate (Scheme 2)
result from the distillation of compound IV). A similar pro-
cess is observed on heating quinuclidine ~V) up to boiling
temperature, in which connection benzoic acid, besides Bill)
is separated (Scheme 3). Heating of the compounds (VI) and (IX)
with phthalic anhydride in the presence of benzene sulfo acid
at 2850 led only to compound (III)(Scheme 4). The structure of
2,3-(3',4'-N-ethy1 piperidine)-quinuelidine was proven by a
counter-synthesis, proceeding from 3-carbethoxy methyl
quinuclidine-2-carboxylic acid. There are 5 references, 2 of
which are Soviet.
ASSOCIATION. Vsesoyuznyy nauchno-issledovatel'skiy khimiko-farmatsevtiches-
kiy inatitut imeni S. Ordzhonikidze (All-Union Scientific
Chemico-pharmaceutical Research Institute imeni S. Ordzhonikidze)
SUBMITTED: January 3, 1958
Card 2/2

AUTIIOqS: Mikhlina, Ye. Ye. , Rubtsov, 1. V. SOV/7(-,-1-19-1-27174
TITLE: Cyano-Ethylation of Quinuclidone-3 (Tsianetilirovnni.ve
khinuklidona-3)
PERIODICALi Zhurnnl obshchey khimii, 1059. Vol 29, 'Ir 1, rp 110-1?' (T-17,R)
ABSTRACT: A very intereatinp problr~m in represented by the cyano-
ethylation of quinuclilone-3 hitherto not inventiratol. Th-
present paper dealq with this question. In i's tran3formition
with an excess of acrylonitrile into dioxane or tertiary butyl
alcohol in the presence of 3C % potpsh lye in methyl Icohol,
a mixtiire of mono- and dicyano-ethylated products in formed.
The general yield of mono- Pnd dicyano-ethylated quinuclilones,
as well as their quantitative relation obtained dependi on the
solvent used. The yield of them tbus amounts to about 44 46 if
the reaction is performed in dioxane. The main product of the
mixture (85 fa) is represented in this case by the dicyano-
-ethylated quinuclidone-3. The substitution of tertiary butyl
alcohol for r1ioxane increases the total yt-ld up to 70 ~41, while
nt the same time also 010 Dercentni-e of monocyano-ethylnted
q-,inuclidone-3 incr-a3es (about 35 4o of the total sum o"
Card 1/3 cyano-eth.,.'Inted pro,iucts). Cn a reaction of q,iinuclilon-~

Cyano-Ethylation of '1~uinijc1j1-,nn-3 SC~V!-70_')n_ 7 /74
with --crylon' ' rllf- at the -.,olnr rntll, th- .741-1 1 Df
products is ~O' t only. On the basis of th- reqctions
formed th- s tructure of formula ( II) wa , assignei to thp mono-
cyann-ethyl,i ted quinucl idone- 5. The reduc t ion -)f ju inucl il no
( IV) yielded the quinuol idine ( VI ) . Th- 9.yn I.hon i,i n-rf or-ned is
presented by scheme 1. 'lie ~icyano-ethylatel q!iin-:clilone-~
can have the str,;cture 2,2- or 13-ethyl cyanid,0-
-quinuclidone-3 3y saponification of the ketnitrile the ket,
diacid is fo",-l The 1-ttnr is riot tr,,nsfor-ie,! into tl~r? tri-
cyclic unoatur,ited co,.i o,ind (A) 7,n he,~tinr -:ith ncnti~ cii
anhydride, which woull bf, the caso if th- ethy! 2ynrjilr~ i7ro,ir,'o
were in position 2 and 4. On the basio of theno data, th-
structurn (VII) is th! only correct one for th.-? iic-~ano-ethyl-
ated quinuclidone-z,. -he juinuclidines (XIIT ~IX), qnd 'X)
the dihydrnziie (XI) and further juiniiclilinrin, X11", (XITT),
and (XIV) were synthof31-.,el from it -iccorlinf- t,) s-'~-no
There are 4 references, ~ -,f which -ire Soviet.
Card 2/3

Cyano-Ethylation of Quinuclidone-3 SOV/79-'9-1-27/-74
ASSOCIATTON: Vae3oyuznyy nauchno-issledovatellskiy khi-iiko-farmatsev-
tichankiy institut imeni 3. Ordzhonikidze (All-Union
Chemico-phprmnceutical Scientific Resenrch Ins*itute imeni
S. Ord7honikidze)
3U KTITTED: November 30, 1957
Card 3/3

50) SUV/79-2)-6-36/72
AUTHORS: Furshtatovs, V. Yn., Mikhlina, fe. fe., Hubtsov, M. V.
TITLEs Synthesis of the Substituted Compounds of the 7-Amiromethyl-6-
(P-aminoethyl)-l-azabicyclo-(3,2,1)-octane (Sirtoz zameahchennykh
7-aviinometil-6-q~-amirioctil)-l-azabitaiklo-(3,2,1)-oktaria)
PERIODICALt Zhurnal obahchey khimii, 1959, Vol 29, Nr 6,
pp 1945 - 1949 (USSR)
ABSTRACT: For the purpose of carrying out the synthesis of the 6,7-di-
aminosubstituted compounds of 1-azabicyclo-(3,2,1)-octane the
hydrochloride -of 6-carboxyLiethyl-l-azabicyclo-(5,2,1)-octarte-7-
carboxylic acid (I) was converted into the corresponding acid
chloride (II) by means of thionyl chloride. The latter wits
reacted with alkyl (aryl) smines and the amides (III) were ob-
tained. The rediction of the amides with aluminum-lithium hydride
led to the substitated compounds of the 7-aminoiaethyl-6-(~-amino-
othyl)-l-azabicyclo-(3,2,1)-octane (IV) (Scheme 1). In t1lie
investigation of the properties of the diamines sjnthesi--ed (IV)
it was fo,;nd that diamines which contain a non-substitated
hydro,gen atom bound,to nitrogen, way be converted into the tri-
Card 1/2 cyclic system 6,7-~3',41-111-alkyl piperidino)-l-azabicyclo-

Synthesis of the :iubstit,~t~-d Co::;~ojndB of the
7-Aminomethyl-6-(~
(3,2,1)-octane (V) in the distillation ir vacuum (Schu:a.., 2). The
formation of the tricyclic system (V) in thia distillation was
confirmed by the opposite synthesis of 6,7-(5',4'-N-bQnzyl
piperidino)-l-azabicyclo-(5,2,1)-octane (V a) according to
schems 3 The 7-bunzyl amino:i,Lthyl-6-(~-oxyethyl)-i-azabici,,;lo-
(3,2,1)-octane (Ref 4) was converted into 7-benzyl arlinomethyl-
6-QS -chloroothyl)-i-azabicyclo-(3,2,1)-octane by :a~ans of thionyl
chloride which yioldijd the coLapound ~,V a) in builing witn p.,ri-
dine. There are 4 5oviut referencea.
ASSOCIATION: Vaesoyuznyy nauchno-issledovatellskiy khimiko-farmat8evtichoskiy
institut imeni S. Ordzhonikidze (All-Union Scientific Choi-io-
pharmaceutical Research Inatitute imeni S. Ordzhonikidze)
SUBMITTEDr May 15, 1~58
Card 2,12

5(3)
AUTHORS: Mikhl-',~.i '~o'
TinEi Syntllonio -f 5-0x~,- '-alky' (-iryl 11-11'1~11'1 I c.
Si nto~ -it h i nu~.' i 11 1-.1 ci kh f
PERIC DICAL: Zhurr-al kliimil-, ': ' ';, -, , -
A.BSTRACT Rubtsov ana P.,jlre( rkc ra d,-7,-~r-.stratel in ~:.-a--L-z trip'rtrl 2)
that some _morlo- tnl :), '-di sub s't 4 t - t,--i .i-' n : 1 i 1'.n( s ai-
high bicluv~ical acli'ilty. With tl~c c' cx-..7,iiur.-, '!,r -r, r
inve sti~;uted 3-subotl tited -:ulnuc I--* il' nc-s, thn uut!., ra :ir-'
ou', the sy n th e si s .- f-i n u 7, !-. --3 3-') x y - a y -I
quirtw~!-'din-s aiA 1,1-Ir ~stu~o. P,-.r "Yj,! !3~r,*l th-
used quinuclidone-3 rhich javc. c Dmpc unds 1 z o a t ii n
orjan, -mLt-,nesitu cor-p~-indo. :1, -1 -1 - I, '. S 1. S tl.~:
J
alcohols r:crs, (,)I L_L~ !j, I ral, 1,, 1 L;h
usr' Cf
q.iinuulid~r--3
."hy, ulnur
I i thiLm 71ai llf;;"l jcl;
rtc, thi ~, a r~g
tert i ai y al 1 s vi th ac: i d
Card 1/2 attairled rl,,(:I" t

Synthesi a of 3-Oxy- (a r~-! I I, I u r rl
and Their Estero
0 1 (1 f,7 r i
solvent th,~ :.c,npuurj 111%) Tr %.9
correspondino, r:a:ly -~rar.~,f if t (11:'
indu---ed t!,e t~, st--dy th, f -ut'
.r.?ag(, n t o -)T. tj,.- 111' lj'~-' J '1~ ~q ' I F thi,n-
ur i I wk!i, u,;, It r, I n
ahort tretmont witi, ti,iow.i e a .14 x 'u.
of 111"1 ) Tri th -iyl Ll - ro'l"i 1:uc I i I I-: f r i
to separate. fleatin,- this riixf',i~ wit*,-, al-, Yd x
yi e Ile d (111a) only. 01- h('Utir-C (11 77 --'t W~ i f u r- i ra
gave (IlIa) in )oa% yif 1,1. '2hi- s
t y h c a t i rig rri' t h 7 ff/., fl -d 1 f '-l r i C -L C r~ t -
resinnus with 80% acid. Cn l!t--atinc (In) f -
thio ny 1 ch I j ri de ( -2 rju i iw) la I- p,- r n
Pormed (S~~hemr~ 2). Mo Cf th,
q,.~in-uclidirics huv~, a:~tjvl
There are 6 f Oilch arr?
ASSOCIATIOM Vaesoyuznyy mauchnco-isslodcvate' -'- ak~ly
institut imeni S. Ori-l:,~i..'kidz~~ I IA' '--Unic-n Sr -,t ',.i 7Y, -mic-n
maceutical Ref3oarch li.F:titul~ imer.. S.
SUBMIT2ED: May 19, 1958
Cerd 2/2

RUBTSGV. M.V.; MIKRLINA% Ye.Ye.g TAKHOUTOV. L.N.
Chemistr7 of quinuclidine derivatives. Usp.khIm. 29
no.1:74-105 Ja 160. (MIRA 13:6)
1. Veeaoyuznyy nauchno-lasladovatellskiy khimiko-farmatsevti-
chuskiy institut Imeml 36 Ordzhonikidze.
Wainuclidiho)

MIMINA. Ye.Ye.: TOROBITICTA. T.Ta.: RUBTSOT. M.T.
Synthesis of 3- and 4-hydroi7piperidine derivatives. ZhtLr.ob.
kblue 30 no.6:1885-1893 J6 160. (KUU 13:6)
1. Tsesqyuzmyy nauchno-issledovatellskiy khiniko-farmateevti-
cheelcty institut imeni S. Ordzhonikidze.
(Piperldine)
to

MIKILLITIA, Te.Te.; RUBTSOV, M.V.
Nov steps tovard the synthesis of 3-quinuclidineacetic acid. Zhurj
ob. khim. 30 no.9:2970-2977 5 160. (MIRA 13:9)
1. Vaeaoyuznyy, nauchno-Issledovatellskiy khimkio-farmateevticheakiy,
institut imeni S. Ordzhonikidze.
(Quinuclidineacetic acid)

JUKUDIA, Ye.yp,; VOROBIYEVA, V. Ya.; RUBTGOV, I.I.V.
Synthesis of p-ilymethylone-bio-quinocludinium halides. Zhur.
ob.khim, 31 no.8:2609-2613 Ag 161. (MIRA 14:8)
1. Vaesoyuznyy nauchno-iesldeovatellskiy khim4ko-farmatsevticheakiy
inatitut imeni S. Ordzhonikidze.
Quinocludinium compounds)
lymethylene cojapounda)
M

HDaUNA, Ye.le.; RUBTSOV, H.V.; VOROBIYEVA, V.Ya.
Synthesis of quinucllding-2. 3--dicarboxylic acid. Zhur.ob.khim.
31 no.10:3251-3255 0 161. (MIU 14:10)
1. Voesoyuznyy nauchno-iseledovatellskiy khimiko-farmatsevticheskiy
institut imcni S.Girdzhonikidze.
(Quinuelidinecarboxylic acid)

KIMLIM, Ye.Ye.; RIJBTSOV, M,.V.
3--Quinuelidi4one in the Knoevenagel reart~on. -..,.ur.ob.khiz.. 3-~.
no.9:293r,~940 S 162. (mm;-- 1~:,))
1. Vscsoyuznyy nauchno-iseledovatellsk-iy khimiko-fnmatsvvtichoqkiy
institut imeni, S. Ordzhonikidze.
(Quinuclidirone) (Knoevenagel reaction)

AUTHORS: Furshtatova, Y. Ya , klkhlina, Ye Te
Rubtsov, M V.
TITLE: The Synthesis of the 6-Carboxymethyl-l-Diazocyclo-(,3,2.i)-
octane-7-Carboxy.'ic Acid and Some of its Derivatives
(Sintez 6--karboksimetil-l-azabitsiklo-(3,2,1)-ok,,an-7-
karbonovoy kisloty i nekotorykh yeye proizvodnykh)
PERIODICAL: Zhurnal ObBhchey Khimii, 1958, Vol. 28, Nr 3. pp. 668-675
(USSR)
ABSTRACT: A number of works is dealing witY. the synthesis and the
biological investigation of the derivatives of quinuclidine.
the I - diazocyclo - (2,2,2) - octane (refs,1 _3). The
dicyclic system isomeric to quinuclidine, the 1-diazocyclo-
(3,2,1)octane, has however, not been sufficiently
investigated until now, Only a limited amount of
6 - monosubstituted 1 - diazocyclo-(3,2,1) -octanes were
obtained. The substituted octanes of the mentioned structure
were not synthetized. Among the 2,3-disubstituted compounds
of quinuclidine synthetized by the authors a number of
Card 1/3 biologically active products was found so that it was also

-
The Synthesis of the 6-Carboxymethyl-l-DiazocYclo-
octane-7-CELrbocylic Acid and Some of its Derivati7es
A.0
of interest/obtain the isomeric 6.7-disubstituted 1-Diazo-
cyclo-(3,2,1) octanes and tj iompare the bioloric-a-, and
chemical properties of the compounds of two isomeric series
with each other, In the present work the synthesis of
6-carboxymethyl - I -diazocyclo-(3,2,1)-oclane-7-carbixy,-~ic
and some derivatives is described. It was carried out
according to the mentioned scheme (see formulae (I) to (X))
Thus the synthesis of 6-carboxymethy'k-l-diazocyclo - (3,2,1)
octane-7-carboxy-ic acid is described The reaction process
is shown as followa: From the ethylester of P-(pyridyl-3)-
acrylic acid passing through the ethylesters of 0-dicarboxy-
methyl-p-(piperidyl - 3)- proprionic acid, 0-carbethoxybromo-
ethyl-(piperidyl -3)-proprionic acid to the diethylester of
6-oa.rboxymethyl-l-diazo-(3,2,1)-octane- 7,7 -dicarboxylic acid.
Together wtth these mentioned products the following com-
pounds are synthetized: 1 . - The diethylester of 6- carboxymethyl-
-1-diazooyole-(3,2,1)-ootano-7-ottrboxylia avid
2.- The di(diethyluminoethyl)- " di-(dimethylaminoothyl)
eater of the 6-carboxymethyl-diazocyclo-(~,2,1)-octane-
Card 213 7-carboxylic acid. 3. 6-.(P-oxymethyl)-7-Oxy-methyl)-d,-ocyc'~o-

The Synthesis of the 6-Carboxymethy-1-1-Diazocyclo- .'g- 28 2 3, 6
octane-7-Carbocyclic Acid axd So7-.e cof its Derivatives
(3, 2. 1 )-octane and 6 (0-chloroe tnyl ) -7 -cri1rrome tt,.Y I -
diazocyclo-(5,2,1)-octane
There are 4 references, 2 of which are Soviet.
ASSL~CIATION: Vsesoyuznyy nauchno-isoledovatel'skiy khimiko-
far-matsevticheakiy institut imeni S Ordzhonikidze (A'---
UniOn 3ciet,tific Che:.ical and Pharmaceutical Reseurcn
lnstitute imeni S. Ordzhonikidze
SUBMITTED: March 16, 1957
Card 3/3

AUTHORS:
TITLE:
PERIODICAL: Z11 11,11;i1 (,'I 1-jrl 11, 1 V I IN: 1,
ABSTRACT:
j I b ed d' 'il. I
I'vom J-411111 wildoll, by rcd- wl-, I'll'I
carrl(-d -,,t witt, u.-,l
11 o ru fo rm .
ON OCOR
t~( ) *clcoA -- (~
N N
Card 1/7

3-(P-AmIn )ben~,,(,~-;Ioxy)- piltoi, ) I-Ilto, w: i.; i., I
veduct Ion of' 3- (p-fil t 1.)X:/ J'j 1 ri1
Raney nickel Tne iame react.1-1-. e v P I.,
,~ a v,~, 3 - ( p - am t i--y ci xa i i -D x-,- ) -il z
3-( rj J.It~- W I
uy hyr1po,)-r~rL.-it-Jon T
- j j Y
(III W:i~; I':- v.
c -I I
solut Ion In lnt~t`lariol
qulnliclidlne (X) wa.,3 form,~~d by r,(-- I i (, t IrC
with 11thlum aluminum liydride. Comp,),i-il (III) wa.~
converted Into 3-(1,' -ca,-bethOKypthr)Y,:,, ) -pI In ~"l i I I
(IV) in thr,,2o diff'-r-nt way.-,: (I N11:-11- (ILL
ht-,ated with anhydro.il;
2 ) N I t r, I I e wa:)
(j, ) Dcj If 'I vvi:; ~b
t. :' (ill "D
y1old -)I, (IV) wa.-, (,()-7'-,%. Th- b-~7t It."
CiLrd 2/7

Syritrie.,,1.,3 -S '6~;
i d by L I -d M- tu'i A
ONI C)4 IC N 01~1,1 INA,
III C141 C~4 CN 'I
(XI
GO'CHpoy, 00010"
N
001),cl ()(CH1115H Ooi'.,~
N
IV) w I tn I It hl,,uri allim I n i.,,, ,iyi,- I J~- 1:, n I.,, t
, wnich c,-L witf, alcc)ti,-,l A,L I a -' I ic ~i i,-, r Id e
M
In benzene gave corresporAinE e.;tf~-r:3 (VI) Tlilonyl
Card 3/7 chloride with (V) courns, 1~,ilrL,Clidifle

SYrithc-,918
of' 3-SubstLtute,i Qliniicil~llr~f-,- T'J7"
~7
(VII). Pie lalter' wit'i I,o~l,)urea anj aftervinj.,~wt~i
alkali is converted Into 3-(
quinuclicline . AcId chluvldo~; ct~act, wtt~i (VIII)
t 111') e.3 L e v.3 .(VII) was heatod with pip.-rIAIne,
morphollne, anJ --JIetIiy1amir~#,. DL t L'I,,st tw(, s
corresponding
XI) anI
II) were ob~ain-d.
R
Pa)
O(N'h
card 4/7
(VII) with diethylamine probably lfoi-rrts a polymert-
compound of (VII). The pharmaccloi-l-~al
was made by K. A. Zaytseva linder- lh- (it, M.

Ca rd 5/11
Tn5 Jo
of
I., if I ri ur
Y,. Id p
Ne it .0
to

7 7i 17
,If.

If 1 74. 17,
loll 114 1
7 1.1 ,2N lit I

77.7
1 1 "s ljl,~ )3
7 1 .5 1 '18 ~,,) 1l)
i -
.,
j 4 Ih -

sy 77
cnntld

y

1 2 1-1.) fir 111.1 11
mis-2(iij 16A
pt 11, 165 -1f.7 .111,i)3N II(A
Call JAII * 7.o F. I ff)2 it). 11 1 )7.N
:a I I..'(
211
11 121 0.. C -. ;'t ..... , A14.1
17 1 fl4N 1 '09 150 N 21,11 ..... 2114.1
F_p'

Synthesis of 3-Substituted Quinuclid1ne 77374
There Is I table; and 5 references, 2 Soviet, 1
French, 2 U.S. Tne U.S. references are. L. H. Stevr-
bach, S. Keiser, J. Am. Chem. Soc., 74, 221--
Ibid. 74, 2211~, (1952)
ASSOCIATION: Ordzhonikidze All-State Scieritlflc-Res(~arch
Pharmaceutical In8itute (V.3e,,;oyuzrkyy na,.icnn~-)-
Issledovatel'skly khlrr~iko-f'ai-inatsevtic.,,c~iikl-" In.-~tIt-it
i-meni S. Ordzhonikidze)
SUBMITTED: January 2, 1959
Card 717

-MIOLIM, It-18-4 RuFfIlsoy 1.1-V
S7Dthesis of , 10 (.~; 21, 2)nonane -2 -a-rbo)ryLic acid, Z~n,:. -, ~
32 no~'7.217'1-2)84 TL 262. ( ~flliA 15 ; ~
1. Vsesoyumyy nauctaia tualedovatel-skly kbiudko- farviatsovtjcho3k.-iy
iTWt'Lt-Ut imCrJ ; (hdZhOrlik!l.2A-.
(Aze h, - ~ yc I ) nonarie )(De,.anol : acid)

KIKHLINA, U.N.; RUBTSOV, M.V.
Reaction of 3-quinuclidinone with hydrazoic acid. Zhu,-.ob.khim.
33 no.7s2l67-2172 Tl 163. (ICRA 16:8)
1. Vaesoyuznyy nauchno-isoledovatellg6iy khimiko-farmatsevticheakiy
institut Im. S.Ordahonikidse.
(Quinuclidine) (Hydrazoic acid)

MIKELINA, Ye.Ye.; VOROBIYEVA, V.Ya.; RURTSOV, M.V.
Synthesis of 2,5-disubstituted quinucliaine. 4i~ir.ob.k~r;im-. 33
no.12:3852-3857 D '63. (MIRA 17:3)
1. Vaesoyuznyy nauciino-issledovatel'skiy kJ.imiko-farnatsevticheskiy
institut imeni Ordzhonikidze.

RUBCOVP M.V. [Fmbtgov, M.V.]; SARAPOV, I.M. [Sharapov, I.M.); MASK(Y-ISKTJ,
M.D. [Mashkovskiy M.D.I; 14ICFUNA,
NIKITSKAJA, E.S. tfl~kitskaya, Ye.S.1; VORORkVA, -Ta. (Torobyeva,
V.Ya.]; USOVSKAJA, V.S. (Usovskaya, V.S.I.
Syrithosli and pliarmacologicaa reaearch on quijiuclidirie, plporillno
and pyridir- If.-Ivntivas. Cesk. fam. 13 no.601~~-315 JTII(4
1. 758E, -, -v-y vWecko-,ryzkumny ustav pro chemli a faxnac 4-1, M(,E;4ve
(VIIICHFI) [Voesoyuznyy nauchno-issledovatel talkly khiv ~Kc-farmatqsv-
tichoskiy institut].

MIMLINA, Yeje.; VOROWYEVA, 'j.Y&.; SHEDGHENKC), V.I.; RUBTSOV, M.','.
Structure of 3-quinucltdinone rearr&ngevlerit pToductB according
to the Schmidt &M Beclunarin reactions. Zhur. org. khlm. I
no.7:.1336-1337 JI 165. (MIRA 18:11)
1. Vaesoyuznyy nauchno-issledovaLellskiy khimiko-f&rwtsevtichoskiy
Institut Imeni S.Ordzhonikidze i Institut khimii prirodnykh
aoyedineniy All SSZR.

4..!XY -qun
r

Sc),,r i,1. V. ; YA10i( TIT( :A:KHL1NA , Y" -ye.
FT BTS C)
nn degrLdation 6'
Hofma L
d1rhiorldo hy moans of a mettifiriol orlution ,f cat.itir ;.otfisr-
1"hur. oi~. khim. 35 nod.:tell Ap 106.
A
'-Isesoyuzny-.v nauchno-issiedov% Ile', I sk'Ly khL:T-iko-fa--ra,sev,Li-
choskiy institLt imeni S. Crdzhoniklcize.

ACC NR, AP6031301 .. - _i SOURCE CODEi-UR/0366/66/002/009/1707/1711
AUTHOR: Yanina, A. D.; YLikhlina, Ye. Ye.; Rubtsov, H. V.
ORG: All-Union Scientific Research Chomical-Pharmacoutical Institute imoni S. Orzho-
nikiclzo (Vsoi;oyuzryy nauchno-ioslodovatollakiy khimiko-farmatsovtichookiy inatitut)
TI?LE: Pinacolone rearrangement in the series of I-azabicycloalkanoo. Part 2
SOURCES Zhumal organicheskoy khimiig v. 2, no. 9, 1966, 1707-1711
TOPIC TAGS: pinacelono rearrangement. pinacol
V%-_AerCC_%je_A%C ~O~C~e conlva"~-A
ABSTW.CTs The reaction of 3-hydroxY-3-carbothoxyquinualidino (I) with butyl and
p-tolyllithium was used to synthesize 3-hydroxY-3-1a,a,-di(p-tolyl)-a-hydroV=othyl)-
quinuclidine (II) and 3-hydroxy-3-(a,a-dibutyl-a-hydroxyinotbyl)quinualidine (III)i
0" OH
"t- C 11 (FOR-Ce.03-n;
C,
N N 0,
(1) (11.111)
The following reactions were also carried auto
Card 1/3 UDCt 5!j7 034.4

ACC NR& AP6031301
C,M,CH
C'H'C)q
C 14401,
Co
C
'0)'o
0
M
OR
CGH%CI41 (VI) A .
(~K C$H"CH3 (VU) R - COCH,
C Ii. CH N110 It H
CH
CS"CM
OR
(Vill. 00
C",
","I I I
I
C CH - C,H, N C14 -C,,Ht
Oil Pt
- P '
C'Hq
C0149
0 49 OCOCH3