SCIENTIFIC ABSTRACT VANAGS, G. - VANAG, G.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R001858520007-5
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: August 31, 2001
• Sequence Number: 7
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

-H, '61
7 T

rhwistry ~nalytic&l
Card 1/1 1 Fub. 11,5 - 6/14
Authors I Vanag., G.
Title I Color reactions of carbazole, indole, pyroUe and some of their
derivatives with brom-ord tro indandi one
PerlOdICRI I Zhtw. anal. khim. 9/4, 217-21%, Jul-Aug )_954
Abstract I The application of bromonitroindandione, for analytical determination
and separation of organic bases and for qualitative identific_~tion
of ce:-ta-in substances by th~_-ir col)r rt~actionq, is ~iscu3sed. In
ice-cold acetic acid offers a ztarac-
teristic coloring wtien in contact with many compounci5 containing
the pyrolle ring. The reaction with carbazole is considered the
most sensitive and the reaction with tryptophan as the most specific.
Reactions with other heterocyclic compounds were found to be perfectly
normal. Three references: 2-LWR and 1-USA (1938-1947). Table.
Institution : Academy of Sciences, Latv-&9R. Institute of Chemistry, Riga
Submitted : -April 3, 1953

rhim--thri4tt- ni 2 mc,h,!~-tithmeae V,;~
Op-
ant9he ke NH#. la~
21r3-2o wxs prepd. by re-jug IV owith *fcOff ;md *M,-d.
tf,Ct), f.-z 5 hm And, D---TrIPL- -

USS,P /C-h or-A Bt, r-7
Card 1/1
Authors Gudrinietee, E. Yu.; and Vanag, G. Ya.
Title Peaction of certain alcohols vrith 2-nitroindandione-1, 3.
Periodical Zhur. 0b. Kh1m, 24, Ed. 4, 725 - 729, April 1954
Abstmet During the heating of nitroindandlone vtth a 1&-ge surplus of isopropyl
-r rimrir-: r! -chr! p IF, re the spl It t incr. of '.he
f7 , .-4 1 .--~ f--.7 . - - i. - - 1. -I,.
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roduce s to n -,o s o I na, a-ro I one F v e i e re i- v,
1 German since 1888; 1 English 1955. T~able.
Institution : Latvian State Univeralty
Submitted : August 31, 1953

US-cR/Chemistry - Synthesis methods
0 lard 1/1 Pub. 151 - 31/37
Authors i Gudrinietse, E.; Uoyland, 0.; ard Vanag, G.
V V"4
Title Nitrodimedone and sorm of its derivatives
Periodical i Zhur. ob. khim. 24/10,, 1863-1866, Oct 1954
Abstract t A new wthod for the derivation of nitrodimedone through nitration of dLmedona
with fumic nitric acid is nr-esented. Certain nitrodi-raedone salts with 'nor-
-ganic and organic bases, well 5:)luole in water and alcohol, are described.
.1
rhe c!erl.vation of chloro- and hrc=_deriV3ti'-Ie5 Of nitrodimedone is explained.
is ~t ann
Institution The Latvian State University
Submittiid May 7, 1954

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VANAGS, G.J.; MATSKANOVA, M.A.
2-nitroindancUons-1.3 asins. Zhur.ob.khim. 25 no-3:580-583
mr '55 (MLU 8: 6)
1. ratvlyv~dy GosudAr*tvemqy,universltst. Rliftskly neditsinekly
institut
. (k,tro'bidandlono)

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PHASE I BOOK EXPLOITATION SOV/19350
Soveahzh&n1ye Vo khImil, takhnologit I primenonlyq pro1xvoJnykh
pirldina I khlnollna. Pisa. 195T
rhin.-ya, tokhnologlya I primeninlye prolzvodny.Lh pirldina I
khln lina, materialy soveshChantra (Chemistry, TeChnolOKY
and otilization or Pyrldlne and QuinolLne Deri~xt ive 81
watorials or the Conference) HIS&, 1xd-YO AN tatviys~'.y
33R. 1960. 299 P. Zrrath 8V - Inserted. 1.000 copies
prIntod.
Sponsoring Agenclext hkademlya na4k Latvlyakoy SM. Institut
khlmll; Vaesayuznoys khlAlcheakoye obahchestro.
Bathamava; Tech. CA.: A. Klyavlnya: Editorial
Zd.
Yu. A. B&nkovskly, Candidate or Chemistry, V. V.
;,'~:
TUL04A. Canlidate or chemistry (Reap. Ed.), L. P. Zalukayvv,
Doctor or chemistry, and x. x. xxin)rn-.
PURPOSE: This book Is Intonded for organic chemists and
a cia engineer*.
COMAQZ: The collection contains 33 articles on methods
of synthesizing or producing pyrIdIne, quinoline, and
tbelr derivatives from natural sour:es. No personalities
are "ntl-Oned. Figures, tables, and references &caompany
the articles.
TAMZ OF COWMYrSi
Q=0_'j?,7E MRr:A-,.-.E.3 07:AL%ED FROL4
TH3 TIMAYJLL Cp-%CKINC) rROZVrT3 op rL*=3

St3-o Tej.e.-,;j2,j Institute)].
B43es Ob-alned Frc. Co&l Tap
lkrtr-v~ A. D, Ak'd~'Jj nau 33SR
k
Tv~%- 31terlan Brinch or the Asademy or scientes uza)j
zx-
tra:tlon a:nI Utilization or Nitrogennool TiLr Bases -on the
3^~ltoklng of Cj"remkhovo Coal 25
Kuxnetsov. V. I., and A

*
P. PaJIV~heva . irnstttut topic-
-
=U
Mmumli Uk
USSR (Melt P~-4r VuXI-neering
Institute of the A~aleny of S:10h,
,
'
-The C*ntn.
of
PYrLd1ne Bases in Tars From. tWe
Themal
Do_
.
,
Oapos Itl h f Lignit-eB F-OM ths DMI*pr Basin 3 T
F~Iito-& L A and a Exnstitut
Lnstitule Of the
Alad~,ty of Sclen2*s L&tviYskaY& SSR)J.Py.-idine Bases prom
Sao-cDelite Tar. L.--__._ 43
nd
fte."I AkaTielt
nxUk S33H 01':!rO.'-"M :nstit.'Te r
U
ttA A~&4e!MY Of 3?1encea 3SR)J. Methods or D-t-er'_1.t lon
"d "~ Ch0r2!'erI4t-'cs of Total .41trogen and N!trog....
B"ovs in rst~"~UMA
Eln8titut gOr7uhikh Z'6kOpA7ec%ykh Akademli
(InAtItute for Mineral P-jels Of the Academ
r f
CZZR)l
SeP~ratlon of the p-plOollne pra~tl
on of
Tar b
the S
l~
tl
e
c
y
vs Extraction Method
69
ZE-Ilt-1,1- A_ and a. pal
11%7311al Chec,_-,jt,y
ror
Oemral Chemlxt
r3r (Warsaw)) Fk
v3loc-h~mjcal Stc_j.," In
P*frldane B49es Prom Products or ~he chemical Procosaing of
75 to

t1tut OrganIch"kego sints,
ta Akademll. nouk.
for OrZanIn.3yn-`hesjx of -the
~~y R (VINtituts Z
r ftlen:jn I&tTly
~
31.7AL35R)j
The TI&naltion
.
Px 1*3- Indandione to Pyridine Derivatives J

USSR,., Chei-iiical Technolo-y. Goe-wical Proijucts and Their 1-13
Application--Treatiiient of solid mineral fuels
Abs Jour: Ref Zhur-Khimiya, Vo 3, 1957, 9214
Author Fedotova, L. and Va,,a,g___I-
0
) 7c
Inst Latvian Academy , eTences
T
Title Pyridine Bases from Sapropelite Tar
Orig Pub: Izv. AN LatvSSR, 1956, No 5, 101-1011 (Latvian
summary)
Abstract: The base content of tar obtained from sapropelite
coal from the SpIgpi swaiip,'Dobel rayon, Latvian
SSR, has been Jiiveutigpted; 9-10%, bases were found
to be present in the tar. It is shown that the
ases consist pri-icJpally of compounds of the py-
ridine and quiriol~ne series. I-To primary means
were found; secondary means were Cletermined to be
present. The art,Lior have invest1gated the pyridine-
picoline fractioi. Five pyridines have been sep-
arated and idei,titied: pyridine, q(-)#-..Ir-

USSR."Chemical Technolog,r. Chemica, Pro6vcts and Their 1-13
Application-Treati-i-,eot of solid mineral fuels
Abs Jour: Ref Zhui,-Khimlya, 110 3, 195'(, 9211!
Abstract: picolims, anc;. 2,6---,titicane. A 10% %S04- sOlu-
tion ertracts onl-, a fraction of the ases nresent
in the tar fractioll.
Card 2/2

ts Sp
c
W-10 1,
Oroup
~-Oksikolo,:iya, 0
'-~,-,ticoat!)ulant action (,,,,l 0-
was -studied on
Lhe
, - -e ?6 --',n`,7;tere(I
durin" it t 1 tat ?-ohe-
m-l
.3 n a
)SO
in I i
alM ion ;I-ac
enapht-enoi t 4, 0 II'l I" -i

VANAG. G.Ya.; SIIARAYA, R-Ya.
t ~1"u;"e~raction of the ethyl ester of chloroindandionecarboxylic acrid
with primary amines. Zhur.ob.khim. 26 no.1:68-74 Ja '56.
(XLHA 9:5)
1. Latviyokiy gosudaretvanniry universitat.
(Indazdionewboxylic acid) (Aminea)

GUMINIECE, J.; DRNIX&HIS. X.J.; MUGS, G.J.
2-nitro-parinaphthindandions-1,3 and certain of Its derivatives.
Zhur.ob.khim. 26 no.1:272-275 Ja 156. (KLRA 9:5)
1. Latviyokiy gosudaretvannyy universitat.
(Banzonaphthenedione)

I/ C- 6- VA
USSR/Organic Chemistry - Gynthc~ic GrZanic-Chenistry E-2
Abs Jour Referat Zhur - Khimiya, 17o 2, 1957, 4341
Author Vanag, G.Ya., Gcyta, L.S.
Title ondensafl"on of Acenaphthe-nequinone with Indandione-1)3.
Orig Pub Zh. obshch. k1hir-ii, 1956, 26, No 2, 511-516
Abstract By condensation of 9cenaphthenequinone (1) with indandi-
one (II) was obtained 2.2-di-(indandione-li, 31-yl-21)-
acenaphthenone-1 (III). On action of Br2 the III is
cleaved and gives 2,2-dibronindandione-1)3 and 2-(21-bro-
rdndandi,)iie-11,3'-Yl-2')..2-broi-,acenaphthenone-1. H2SO4
reacts w..'u-h III to cive 2-i,.lda-idione-11,3'-ylene-2-acena-
ph-thenon-!-l (111). To a solution of 3 g I in 80 m! glacial
CH3COOH Is added a soluticn of 4.8 g 11 in 20 r.11 glacial
C1[ C0011 arA 1 ml --micentrated 1101, the mixturc i,
brought to a boil and'heated for 3 hours: there are o'btai-
ned 6 4 j; III, UP 2.35-2360. Prepared were the K-, piperi-
dine and ethylaraine salts of Ill. 4 g III are shaken
Card 112 .. 55 -

USSR/Organic Chemistry Synthetic Organic Chemintry E-2
Abs Jour Referat Zhur - Khimiya, No 2, 1957, 4341
for 15 minutes with 40 mi concentrated 112SO4, the fil-
trate is poured into 300 ril water, there are obtained
1-95 9 IV, DT 191-1920 (from chloroform), 0.2 g IV hea-
ted with 10 ml alcohol and 0.1 g II are added, obtained
0.29 g III. O.r- g IV dissolved in 10 rl CHC1 and Mded
a solution of 1 P-1 Br2 in 4 ra CEC1 obta nel 0-3 9
dibromide of IV, MP 251...2030 (froin Lnzcne). on action
of Li-dust on the dibrcmide there is formed the initial
IV. Heating of 1 g IV aLd 20 ml of a 20rfj solution of
N2H4'H2 0 give-s 0.8 g azine of IV, DIP 255-2560
Card 2/2 - 56 -

0-1 A,
IL
USSR/Organic Chemistry. Synthetic Organic Chemistry. E-2
Abs Jour; Rof Zhur-Khimiyat No 6, 1957, 19151
Wthor Vanag G. Ya., Gciyta L. S.
Inst
Title Cyclization of 2,2- diindandionylaconaphthonono -1.
Orig Pub: Zh. obshch. khimiyi, 1956, 26, No 6~ 1746-1749.
Abstract- Acomplitnc.-nona-1--spiro-(2,41)--2',31(c))-61, 51-(c))-
dibonzoylonapyrano (I) is synthasizad and its intor-
action aith T
'13 nnd aminos is studied. To a solution of
1 9. 2 2-diidandionylaccnaphthanona-1 (11) (RZM~him.,
19571 ~341) in hot (C11300)20 is added 2 drops of conc.
H2SO4, hoatod 45-50 min., thr, prucipitato is washed with
glacial C113COOH and alcohol and I is obtained, yiold
89.51., m.p. 3600 (from pyridine).
Card 1/2

USSR/Organic Chomistry. Synthotir. Organic Chordintry.
Abs Jourt Rcf Zhur-Khimiyaj No 6, 1957, 19151
C A~
C
L-2
Oyclization occurs as a rosult of splitting off of wator
frora the onol forra II. On boiling with an alcohol solu-
tion of 1"011, 1 is transforr-od into 11 0.2 g. I and 5 cc
of liquid ITH in a --alod tubc nroleft standing for 24
hours at -- Lo vu I U
, accnaphthcnono--l-s-,iro-(2,4 )-2 '3' (CO),
61,5'(C)) dibcnzoylono-1,4'-dihydropyridino (III) is
obtainod, crystallyzing with 1 nolocti'o of TM3, yiold
0.19 g.; it docompocon at 1660; aftor splitting off MI.,
2
m-P. 374-3760 (from ale.), 1 g. I is boilod 15 min. with
2 cc anilino and 20 cc glacial CH3COOH, IT-phonyl-III, is
obtainod, yiold 51.3%, m.p. 3500.
Card 2/2

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GUERJ]IftBTSB. I.Yu.; DMffMIS. Mg.; VANAG, G.Yot.
Sulf onation of A-diketones b7 d1oxane su-Ifurtrioxide DokI.AM SSSR
110 no.5:786-788 0 156. in: 1)
1. Lfttviyokiy gosudarstvennyy universitet. PredetpAvleno akademikom
I.N,N~sarav'ym, i
(Ketones) (bulfonation) (Sulfur organic compounds)

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VANAG, G. Ya, ; DUBUR, G - Ya.
Imins of di- and poly-ketones. Part 2: Trisindandione. Zhur.ob.
khim. 27 no.10:2729-2733 0 157. (KIRA 11:4)
l.Latviyskiy gosudarstvenny7 universitete
(Indandione)

I - - - -VAINAG, G. Ya. ,- STAKU I CH, - E. I. ; GRU, E. Ya.
Imins of di- And poly-katoneg. Part 3: Benzalindardions. Zhur,ob,
khim. 27 no.10.#2733-2736 0 157. WRA :Ei:4)
l.Latviyskiy gosudaretvanny7 universitato
(Indandione)

GUMINIETSE. E.; IMYIAND, 0. *, VAMG, G.
Iodonlum derivatives of A-diketones. Part 1: The reaction of
dimedon with iodozobenzene. Zhur.ob.kh1m. 27 no.10:2737-2740
0 '57. (MIRA 11:4)
l.Latviyakiy gosudarstvennyy universitet.
(Cyclohexnedione) (Benzene)

Y
ly~
G-
A
AUTH/40J~ ?Zdriniyetse; E. Yu. Kurt.,A-,:.,n,. D. K.
Vanag, G, Ya.
TITLE: 2-Nitro-5-Phe-iy-,cvolo'nexarid-*.o,-i --1., 3 and i--.s Der.-iati.--res
(2-Nitro- 5-feniltsik-logeksandion i ye6o
proizvodnyye).
PERIODICAL: Zhurnal Obahchey Khimi--', 1957, Vol. 27, Nr 11,, pp. 3087-3092,
(USSR)
ABSTRACT: In connection with the authordinve9tigations in the field
of the nitroderivati-ves of cyclic fi-d1iketcn;-,- they examined
5-phenylcyclohexandien - 1,3 wh,~ch in its resembles
5,5-dimethylcyclohexandion -1,1, The nt-troderivati-re of
this hexandion was hitherto unknown, -~--,-,Ye.-i:tlcy,-.!,.Ihexardion
1,3 is produced by conden.9abion of benzei.9:1~cli'cPe Wir-h
malinic ac.,d residue3. The authors im-roved the. method
described in publications by reducing dura'--"o-a of
condensation from 7 hours to 15-'0 minutec. 2he product
obtained in sufficient purrity did not ne,-~d t:? te
recrystallized. The nitration took plla~:~- accordjr.F to the
I)-dimethyle
pattern used in the cane of 5~
Xj
The aqueouo bolution of the nthe3lzed 2-nixro-1)-phonyl-
Card 1/2 cyclohexandion -,. (I
. '~ has 3-'rong acid prcpert.,-vz, ani d4splaces

/1, ~
2-Nitro 5-Phonyloyclohexandion _1,7 and jt5 0
Derivatives
the carboniz acid from the carbonates, like hydr1-4;er.
sulfide from sulfides. Therefore the salt fornation easily
takes place. Some salts of nitropliertylt.,yolo~,.,?xaiidi.oii liith
orC,anic bases were produced. Thus the synihesi3 of
5-phenylcyclohexand3.or -.1,3 was :Lmproved and ';--niTro
5-phenyloyclohexandion -1,1 hitherto not described ir.
publications was obtained. The following deriv~~t-,ves of
thi3 compound vere also prcdu,;ed.: salts ar-orFar-is and
organic bases; 2-halogen -2-nitro -5-phenyleyzicnexandion
-1,31 monosemicarbozone, the monoxim, and the hydrojen chloride
salt of 2-amino - 5-phenyleyalchexandio-n -1,3~
There are 1 table. and 19 referenses, 4 of which are Slavic.
ASSOCIATION: Latvian State Univeraity (L;itviyslziy gosudarqtvennyy
univer3itet),
SUBMITTED: October 31, 19~6
AVAILABLE: Library of Con.-ress
Card 2/2 1. 2-Witro-5 phenyleyelohexandion-1,3-Derivatives

AUTHORS: Geyta, L. S., Vanag, G. Ya. 79-11-42/1;S
TITLE: Compounds With two Heminal Indandione-Groups in the
Molecule (Soyedineniya s dvumya geminalInymi indandionovymi
gruppami v molekule).
PERIODICAL: Zhurnal Obshchey Khimii, 19571 Vol. 27, Nr 11,
pp. 3109-3114, (USSR)
ABSTRACT: It was found that in the reaction of indandione-1,3 with
phenanthrene-quinone and acetonaphthene-quinor-e a
carbonyl-group of these quinones condenses with two
indandione-molecules, where 1 water molecule is separated
and a diindandionyl derivative Is produced (see formulae).
In this manner one comes from the easily accensiblQ
quinones and indandione to complicated heterocyclio
compounds. It was of interest to determine whether haminal
diindandionyl-derivatives with simpler radicals behave in
an analogoua manner. In the attempts to couple indandione
into different aryliden.-Indandiones it was found th~-tt these
reactions also proceed in the same way as the above-mentioned
ones. Thus benzalindandione and nitrobenzalindandiones unite
with indandione on the double bond and form compounds
Card 1/2 possessing two indandione-groups in the case of one carbon

Compounds With two Heminal Indandione-Groups in the Molecule 79-11-42/56
atom. Benzalindandiones having nucleophilic substituents in
the arylidene-group do not unite with indandione. By the
action of the acetic anhydride and in the presence of
concentrated sulfuric ac'j.d the heminal diindandionyl-
compounds split off one water molecule from both 4nr,!-
hydroxyl-C;roups and are converted to derivatives of pyrone.
By the action of aniline these derivatives receive nitrogen
instead of the oxygen brfldge and form the corresponding
N-phanyl-derivatives of dehydropyridine.
There are 16 references, 5 of which are Slavic.
ASSOCIATION: Institute of Chemistry AS Latvian SSR
(Inatitut khimii Akademia nauk Latviyskoy SSR).
SUBMITTED: October 24, 1956
AVAILABLE: Library of Congress
1. Indandione - 1,3 - Condensation reactions
2. Phenanthrene - Quinone - Ccndersqtion reactions
Card 2/2 3. Acetonaphthene - ;4uinone - Cona--r,.;,jttcn reactions

VANTAGS, G.
GUIRRAL
pp,RIODICALS: VESTIS, No. 1, 1958
UNMS, G. Some derivatives of 2-dirlienylacetylindanoine-1, 3. In Ruasian.
P. 107
- onthly list of East D;ropean Accessions (E~:.Al) LC. Vol. 3, NO. 2,
February 1~-,59, Unclass.

UNAG, G.Ya..; AREN, A.K.
Xanthylindandione. Xhim. nauka i prom. 3 no.4:537-538 '58.
(14IRA 11:10)
l.Latviyskiy gosudaretvenny7 universitet.
(Indan)

SOV/156-58-4-34/49
AUTHORS: Gudr-'niyetse, E. Yu., Iyevin'sh, A. P.,.,Van j,,G..,_Ya.
TITLE: The Sulfiirization of Cycliz P-Diketones With Sulfuric Acid in
the Presence of Acetic Anhydride (Sulifl--cr1r~Yu tsiklicheskikh
P-diketonov sernoy kialotoy v prisutstvii uksusnogo angidrida)
PERIODICAL: Nauchnyye doklady vys3hey shkoly. Khimiya i khimicheskaya
tekhnologiya, 1958, Nr 4, pp 746-750 (USSR)
ABSTRACT: The following cyclic P-diketones were sulfurized with qb~
sulfuric acid in the presence of acetic anhydride: 5,5-dimethyl
cyclohexanedione -1,3; 5-phenyl cyclohexaneaiore,,-1,3; indan-
dione-1,3; 2-phenyl indandione-1,3; perinaphth-indandione and
bindon. The sulfurized 0-diketones were separated in form of
sodium or potassium salts. The mechanism of the sulfurization
with sulfuric acid in the presence of acetic acid probably
proceeds according to intramolecular rearrangements. At first
a dark-red colored product is formed. After 5-15 minutes a
white deposit (III) precipitates.
Card 1/2

SOV/156-58-4-34/4~
The Sulfurization of Cyclic P-Diketones With Sulfuric Acid in '.he Presence
of Acetic Anhydride
?03
H4 CO -" CH2+ 2 SO-L-~.. C6H4-,-CO-,- CH2C6H4.-Ico " C(so3H)2
CO'/ CO "-COI/
s03 111
IV
There are 1 table and 1~ references, 4 eX which are Soviet.
ASSOCIATION: Kafedra organicheskoy khimii Latviyskogo gosudarstvennogo
universiteta im. Petra Stuchki (Chair of Organic Chemistry
at the LatviaMState University imeni Petr Stuchkg~)
SUBMITTED: April 28, 1958
Card 2/2

VANAGS, G. -4
GENERAL
FERIODICAIS: VESTIS; No. 5p 1958
VINAGS, G. Pyridazines bases of sepropelic tar. II. In Russian. p. 93
Monthly list of East European Accesidons (EEAI) W, Vol. 8, No. 2,
February 1959, Unalass.

VAIJAGS, G.
momm
GENERAL
PEMODICALS: VESTIS, No. 5, 1958
VANAGS, G. Obtaining 2-nitroindandione-1,3. In Russiaa. p. 101
Montbljt list of East European Accessions (EEAI) LC, Vol. 8,, No. 2,
February 1959, Unclass,

VANAGS- G IQZXr-31, GBfftl--T,.
GENERAL
PERIODICAIS: VESTIS; NO. 6; 1958
VANAGS-., G. ; Lft*-t-V- GSH*r~L- 4p5-dimot~oxyindandione-ld-
In Russian. p. 119.
Monthly list of East Eurupean Accessions (EEAI) LC-, VOL. 8p No* 2)
February 1959. Unclass.

YAUG9.-A.. Go ;i - Doff
GEMMAL
PERIODICAIS: VESTIS-., NO. 8,. 1958
VANAGS-1 G. ; KQFT
,M~07AV=Hr Experimental study of the anticoag-
u1sint, properties of some indandiono-1.3 dorivativeop In Rwaian.
PO 930
Monthly list of East European Accessions (EEAI) L C-f VOL. 8, No. 2
February 1959p Unclass.

AUTTIORS: Vanag, G. Ya.,Lukevits, E. Ya., 75-13-2-19/27
TITLE: Qualitative Reaction for m-Aminophenol and p- A=ino-
salicylic Acid (Kachestvennaya reaktsiya na m-aminofenol
i p-aminosalitsilovuyu kislotu)
PERIODICALi Zhurnal Analiticheakoy Khimii, 1958, Vol- 13, Nr 2,
pp. 253-254 (USSR)
ABSTRACT- It was found by the authors, that green fluorescence
occurs in the boiling of a solution of m- aminophenol in
glacial acetic acid with 2-nitroso-indandone 0,3). If the
concentration of the m-aminophenol is sufficiently high,
thqcolor of the solution changes to red. If the concentration
of m-amino-phenol is very low, the fluorescence occurs only
after cooling the 3olution. A small excess of nitroso-
indandone (up to 3 mole per mol of m-aminophenol) favors
-the reaction, a great excess of the reagent somewhat redUces
Card 1/4 the sensitivity.

75-13-2-19/27
Qualitative Reaction for m-Aminophenoi and p- Aminosalicylic -Ac--;d
CO
C6H4 < > CHNO ~~-C 6HKCO ~' C. NOH
CO CO
The maximum dilution of m-aminophenol at which fluorescence
still occurs amounts to 1: 40000. In ethyl alcohol, ether,
benzenef dioxane, diluted acetic acid and even in glacial
acetic acidcontaining a small amount of actic anhydride no
fluorescence occurs. 0- and p-aminophenol give no similar
reaction and therefore have no disturbing influence up to
a hundred fold excess as compared to m-aminophenol, At even
greater amounts of o- and p- aminophenol the solution
changes to bright red and no fluorescence occurs. Phenol,
resorcin, aniline and riany other aromatic and aliphatic
primary, secondary and tertiary amines with nitroso -indandone
give no fluorescence,therefore the reaction being specific
for m- aminophenol. As is known, p-aminosalicy'Lic acid (PAS)
is easely decarboxylated on heating, forming m-aminophenol.
Card 2/4 It had to be expected therefore, that PAS gives a positive

75-13-2-19/27
Qualitative Reaction for =.- Aminophenol and p-Aminosalicylic Acid
reaction with nitroso-indandone. A splitting off of CO 2
actually occurs at a heating of PAS with nitroso-indandone
glacial acetic and gradually the liquid begins to fluoresce
with a green color. With small amounts of PAS heating must
be prolonged, because the decomposition of PAS does not
proceed instantaneously. The maximum dilution of p-amino-
Balicylic acid, at which a fluorescence still occurs, amounts
to 1: 28000. The ratio of the sensitivity of the detection
of m-aminophenol and of PAS (40000 : 28000) approximately
corresponds to the ratio of the molecular weights (153:100.).
Prom this follows, that PAS under the conditions of the
reaction almost quantitatively decomposes into m-aminophenol.
The representation of 2-nitroso-indandone (1,3) in small
amounts (reference 1) and in greater amounts (reference 2)
and the performance of the detection reactions is accurately
Card 3/4 described.

75-13-2-19/27
qualitative Reaction for m-Aminophonol and p.-Aminosalicylic Acid
There are 4 references, 1 of which ia Soviet.
ASSOCIATIONt Latviyskiy gosudarstvennyy universitet,Ri.-a ( Riga,
Latvian State University)
SUBMITTED: November 5, 1956
1. Phenols--Chemical reactions 2. Aminosalicylic acid--Chemleal
reactions 3. Aminosalicylic acid--Temperature factors 4. Amino-
salicylic acid--Decompos'Ltion
Card 4/4

AUTHORS: Vanag, G. Ya., Matskanova, M. A. SOV/75-13-4--20/29
TITLE: Color Reactions of Nitroindandione (Tavetnyye reaktsii
Nitroindandiona) Communication II. Reactions With Indolez
and Carbazole (Soobshcheniye II. Reaktsii s indolami i
karbazolom)
PERIODICAL: Zhurnal analiticheskoy khimii, 1958, Vol. 13, Nr 4, Pp~ 485-
486 (USSR)
ABSTRACT: 2-nitroindandione (',3), C6 H4-(CO)2'CH-NO2 yiels a number of
color reactions With organic compounds (Ref 1), which fact may
be made use of for determinations. Pyrroles with nitroindand-
ione yield red or orange colors in aqueous, alcoholic and
acetic solutions. The authors of the present paper investi-
gated the reaction of nitroindandione to compounds containing
the pyrrole ring condensed with other rings. Indole and its
homologs with nitro--indandione yield a very deep red color al-
ready at room tempe-,.1ature. The maximum dilution where the col-
or can still be noticed is 1t333 000 for indole. Heating ac-
celerates the forma-,ion of the color a little. When the indole
Card 1/4 solution is not dilated to a great extent a red precipitate is

SOV/75-13-4-20/29
Color Reactions of Nitroindandione. Communication II. Reactions With indcles
and Carbazole
separated especially on heating. The results obtained from the
analogous investigations of 6 indole homologs are The
most sensitive reaction with nitroindandlone of a 11 compounds
investi,--ated was obtiined with 7-methylindole, which YiElds a
red color which occurs in the case of heatin- even to a dilu-
tion of 1:5 000 000. As is known various samples of mineral
oil contain porphyrin (Ref 2). Besides these porphyrins also
pyrroles and indoles must be present. Mineral oil with nitro-
indandione actually yields the colors characteristic for in-
doles and pyrroles. Carbazole with nitroindandione in alcohol-
ic solution displays an orange color on heating; the maximum
dilution is 1;20 000. It was shown already earlier that also
2-bromo-2-nitroindan(lione (1,3) yields color reactions with
pyrrole3, indoles, and carbazole; the reaction with carbazole
has the greatest sensitivity, while indoles and pyrrole3 react
less sensitive. Also the reaction of bromonitro indandione
with tryptophane, whereas nitroindandione with tryptophane
does not yield .--I color reaction. The two reagento therefore
supplement each other. For the purpose of cl.ecking a solution
Card 2/4 of the substance to be investigated is shaken in alcohol,

SOV/75-13 -4 - 201,20,
Color Reactions of Nitroindandione. Co'77unication II. Reactions il-ti:
and Carbazole
glacial acetic acid or water with nitroindandione in solid
form or in form of a solution. In the presence of indolos and
pyrroles a color is quickly developed which is usually red or
red-violet, And in the case,of a high dilution it is orange.
If no" color is displayed the solution is heated. If the color
is shown only on heating either indoles or pyrroles are pres-
ent in very small concentration 'a,,or there are.indoles present
which are substituted in position 2 or 3, or it is carbazole.
Heteroauxin (3-indolyl acetic acid) badly reacts only little
with nitroindandione. The red coldr formed on the heating of
the acetic solution probably is caused by decomposition prod-
ucts. There are.1 table and 3 references, which are
Soviet.
ASSOCIATION: Latviyskiy gosudarstvennyy universitet i Rizhsk4-y meditsinskiy
institut (IlAtTian State University and Figa Medical Institute)
SUBMITTED. October 6, 1956
Card 3/4

SOV/75-15-440/29
Color Reactions of Nitroindandione, Co-,muication II, Reactions With Indol.(;-a
and Carbazole
1. Pentanedione-Chemical reactions 2. Indoles--Ghemical reactions
3. CarbazoleB--Chemical reactions 4. Dyes
Card 4/4

lip
XX~W~N
Hn
Y A JV4 (4,
79-1--13/63
AUTHORS: Gudriniyetse, E. Yu. Vana,-, 0. Ya.
TITLE: Investigations in the Field of Cyclic Arylazo-P-Dil-etones
(Insladovaniya v oblasti toiklichaskikh arilazo- diketonov)
I.'I'he Condensation of Indandione-1,3 With Diazo Lmpoands
(I. Kondensatsiya indandiona-1,3 s diazosoyedineniyami)
PERIODICAL: Zhurnal Obshchey Khiriii, 1958, Vol. 28, Nr 1, PP-58-62(USSR)
ABSTRACT: In the present experiments the authors connected indandione.,
-1,3 with different diazotized amines and their derivatives.
The reaction takes place most rapidly in an alkaline, some-,
what more slowly in a neutral and most slowly in an acid me-
dium. But the final products are most purely obtained in an
acid medium. The conversion of indandione with diazo salts
in an acid medium is unknown, on the contrary it is pointed
out in publications that cyclic diketones only react in this
manner in an alkaline medium. The products of the conversion
of indandione with diazo compounds - arylazoindandiones - are
Card 1/3 crystalline compounds and diffioult to dissolve in ordinary

% 79--l-13/63
Investigations in the Field of Cyclic Arylaze-P-Diketones. 1. The Cond-insa..
tion of Indandione-1,3 With Diazo Compounds
solvents, especially in glacial anetic acid, dicza-ne ---,d
acetone. The table enurierates the products of the reaction
of indandione with diazotized aromatic amines. 2-phenylazo-
indanione-1,3 was more thorouGhly investigated. It is pos-,
sible that the name of this compourd does not correspond
to its structre, as, accordinj to published data, it pos--
sesses the structure of phenylhydrazone. The authors for the
present are of the opinion that phenylazoindardLone exists
in two tautomeric forms (formulae I and II) which are in
equilibrium. Accordin- to conditions the hydrazo- or the
U
azo-form (I and II) reactz. In favor of formula II speaks
the solubility of phenylindandione in alkali, under the for-
mation of essolates which re-form the unchanged phanylaze-
indandione (II) on acidification. Thus the most favorable
conditions for the synthesis of 2-phenylazoindandione-1,3
have been determined and a number of other 2-arylazoindand-
ione-10 viere synthesized. Some derivatives of phenylazo-
indandione-1,3 were produced, toot p-bromophenylazoindandicre,
p-.nitrophenylazoindandione, p-sulfophenylazoindandione, the
Card 2/3 monoxym of phenylazoindandione, pheny1hydrazone and tha azine

V /YA
79-1-20/63
AUTHORS*. Gudriniyetse, E. Yu. , Iyevin'sh, A. F. Vana-7, G. Ya.
TITLE: The Sulfonation of P-Diketones With Dioxane-Sulfotrioxide
(Sul Ifirovaniye P-diketonov dioksan - 3ullfotrioksido-'I)
II. indandione-1,3-Stilfonic Acid-2 and Its Salts (II. IndBM-
dion-1,3-sullfonovaya-2 kislota i yoyo Boli)
FERIODICAM Zhurnal Obshchf~', Vol.28, 1Tr 1 PP-95-100(USSR)
ABSTRAM In the precedinG paper it was .9hown that indandjone-1 3 is
easily sulfonated witti dioxane-sulfotrioxide (- D - SO ) on
which occasion indanione-1,3-3iilfonic acid-2 is produced.
In publications it is maintained that the 3ulfanation pro-
ceeds over the enole form (see fcrmula (I)), on which occa-
sion the addition product is then formed, which finally in
the hydrolYsis yields the sulfonic acid in our case (.see
.the process of reaction). It was, however, not possible to
isolate the intermediate product (II). On addition of the
indandione to the solution of 1) - SO a reaction immediate
1y takes placet the dissolved substil-ce warms up (coolinc.;
Card 1/3 with water!) and after 2 - 3 minutes indandione-i,3-sulfo-

79-1-20/63
The Sulfonation of P-Diketones With D4,oxane-Sulfotrioxide. II. Indandione-
-1,3--Sulfonic Acid-2 and Its Salts
nic acid-2 (III) is 1weripitAed. The solution of this preci-
pitate in water dOO13 Y t show any reaction to the sulfate-
-ion from which follows that the asnumod intermediate pro-
duct (II) does not form. It seems that this reaction takes
place im;iediately wit'A the ITdrogen of tho active methyl
gxoup of indandione-1,3 tbat in other words the indandione
joins the sulfuric-anhydride molecule under the formation
of indandione-1,3-sulfonic acid-2 (III). In the case of an
excess of D - SO and at elevated te-ireratures indandione-
-10-disulfonio Lid-2,2 (IV) in produced which is isolated
as a sodium salt. The crystallized indandionsulfonic acid
(III) could not be recrystallized. - Thuu it was proved that
the indandioneulfonic acid in contrast to 2-nitraindaidione
i3 easily converted to the enole-forn and that either cmiy
one sulfo group or the sulfo group together with the enole
group 1wticipate in its salification. The cobalt-, nickel-
and manganese-salts cf indandionsulfonic acid form complex
compounds with pyridine. There are 6 references, 5 of which
Card 2/3 are Slavic.

79-1-20/63
The Sulfonation of P-Diketones With Dioxane-Sulfotrioxide. II. Indandione-
IP3-Sulfonic Acid-2 and Its Salts
ASSOCIATION: Latvian State University
(Latviyskiy gosudarstvennyy universitet)
SUBMITTEDt -December 24, 1956
AVAILABLEz Library of Congress
Card 3/3 i. Ghemistry 2. Sulfones

79-28-5-14/69

AUTHORS: ,2&,,Y _,Pudriniyetse, E. Yu.
Neyland, 0. Ya~, Vana&j,'
TITLE: Iodonium Derivatives of P-Diketones (Yodoniyevyye proizvodnyye
P-diketonov) II. Thermal Decompooition of the Phonyldimedonyl-.
iodonium (II. Termicheskoye razlozheniye fenildimed,)nilyodona)
PERIODICAL: Zhurnal Obshchey Khimii, 1958, Vol. 28, Nr 5,
pp. 1201 - 1205 (USSR)
ABSTRACT: Earlier (Reference 1),the authors had shown that the dimedo-
nium (5,5-dimethyleyelohexandion-1,3) reacts very easily with
iodosobenzene with the formation of an iodonium compound -
-phenyldimedonyliodonium (formula II). The recrystallized and
dried product is very stable at usual temperature, contrary
to the non-purified one. But also the purified product (11)
decomposes on boiling in aqueous solutions. From the decompo-
sition products.iodized benzene and the phenyether of iodo-
dimedon (III) co,uld bt3 separated, the composition of which is
proved by cleavage with acids in phrenol and conversion into
Card 1/3 the phenyl ether of dimedorm (IV). This ether is easily cleft

79-28-5-14/69
Iodonium Derivatives of P-Diketones. II. Thermal Decomposition of the Phenyl-
dimedonyliodonium
into phenol and dimedone by acids. The decomposition of
phenyldimadonyliodonium is illustrated by scheme 1. Depending
on the place of the break of the C-J bindine,the phenylether
of iododimedone iodized benzene are obtained. The investiga-
tion on the decompositionof 2.henyl dimedonyliodonium shows
clearly that this compound nui; the structure of iodonium salts.
The phenYl ethersOf dimedone have hitherto not been described~
Thus in the thermal decompositionoi,)~enyl dimedonyliodonium
a new compound forms, namely,the pheny.L etnelbf iododimedone,
besides,still-iodized benzene and an oily product of unknown
structure. In the reductiop of phellyl ether of the lododimedone
a new product, the phenylethdr of diriedone was obtained. In
the case of direct phenylation of dimedone v(ith diphenyliodonium
bromide now products resulted: the phenyl ether of dimedone,
the phenyldimedone, the diphonyl dimedone and the phenyl dVaer
of phenyldimedone. There are 8 references, 2 of ~-.rhich are
Card 2/3 Soviet.

79-28-5-14/69
Iodonium Derivatives of P-Diketones. II. Thermal Decomposition of the
Phonyldimedonyliodonium
ASSOCIATION: Latviyskiy gosudaretvennyy universitet (Latvian State Uni-
versity)
SUBMITTED: April 15, 1957
Card 3/3

ATI.THOM ,Xaa!Ej_2,_ja,"shkaya. V. P. SOV/ 791-28-6-18/63
TITLE: 4-Nitroindandione-193(4--Nitroindrtidion -1,3)
PERIODICAL: Zhurnal obshchey lhimii, 1958, Vol. 28, 11r 6,
P,P- 1520 -- 1524 (USSR)
ABSTRACT: Among the indandione-1,3-derivatives physioloGically active com-
pounds as well as rea0ents of Creat analytical Yalue were found,
the latter remark applying especially to the analogs of the in-
dandione. In looking for new analytical reagents in this group
the authors believe thatk different from those already knovm,
various functional jroups can 'be introduced to the benzene ring
of the indandione which fact has hitherto beLn little used. Based
on theoretical considerations the indandione derivatives with a
negative (electrophilic) substituent in the benzene nucleus might
be of special interest, which also was the reason for preferring
the synthesis of 4-nitroindandione-1,3 to the others. Of the two
known syntheses of indandione-%3 only the one could be taken
into account which connistz of the condensation of the phtidic
anhydride with acetic anhydride and the isomerization of the ib-
tained phthalic acetic; acid by sodium ethylate to the irdandione
Card 113 (see scheme 2). In the present case, however; th~_ acetic anhydride

4-gitroindandione-1,3
30V / 79-2a-6-le/63
had to be replaced by malonic acid and the condensation had to
be carried out in pyridine in the presence of some drops of
piperidine at low temperature in order to obtain the nitrophthalic
acetic acid (see scheme 3). The isomers which had to be theoreti-
cally expected did not have to be determined as they had to yield
one and the same product in the regrouping, viz. the 4-nitroin-
dandione-i,3 (IV), which was proved by the experim.,nt, This final
product does not crystallize well, it dissolves with an orange
color in alkali liquor and on acidification in again separated as
initial product. On heating with water the 4-nitroindandione-1,3
turns red-violet. The dioxime (V) proves that it contains two
carbonyl groups. The product of the conversion with benzaldehyde
(VI) points to the presence of an active mothylene group. Thus
the formula (IV) set up for the 4-nitroindandione-1,3 does not
cause any contradictions. There are 6 references, 3 of which are
sovi3t.
ASSOCIATION: Latviyskiy gosudarstvennyy uniYersitet i Rizhskiy khimikofarmatsev-
ticheskiy zavod (Latvian State Univernity and Riga Chemical-
Pharmaceutical Pactory)
SUBMITTED: June lo~ 1957
Card 2/3

IF -
- 4-Nitroindandione-l,.'
1. Reagents--Sources
SOVI 79-28-6-16163
Card 3/3

AUTHORS: Matakanova, M. A.j Vanag, G. Ya. SOV/79-28-10-34/6o
TITLE: I-Amino Y2thyl-Phthalazono-4(1-Amino:zietil-ftitlazon-4)
PERIODICAL: Zhurnal obshchey khimii, 1956, Vol 26, 11'r lo,
pp 2798 - 28o1 (USSR)
ABSTRACT: In the reaction of the hydrazine hydrate with 2-nitro-
indandione-1,3 the authors (Ref 1) obtained the
1-nitroqmethyl phthalazone-4 (I). As the derivatives
of the phthalazone have been proved many times to be
physioloZ;ically active compounds it was of interest
to obtain some derivatives of the nitro-methyl
phthalazone. The authors reduced it to obtain a water
soluble compound. Hydriodic acid together with red
phosphorus proved to be the best reducing agent; the
nitro group is easily reduced to the armine 6roup and
the forned amino methyl-phthalazone (II) is separated
in form of hydrogen iodide salt. A nitro-indandioniLte
(Ref 3) which is difficult to dissolve, is a compound
with a primary amino group; it reacts with phthalic
Card 1/'~ anhydride (Ref 4) under the formation of compound (III).

1-A,mino Methyl-Phthalazone-4
SOV/79-26-10-34/60
On the action of benzoyl chloride in alkaline medium
on I-amino methyl-phthalazone-4 the compound (17)
is formed. The form (VI) is the most probable of the
three forms possible of this compound (V-VII). From
the fact that also 1-phthalimid* methyl-phthala-zone-4
yields an acetyl derivative (XIII) in form of colorless
crystals it may be seen that the amino group of -the
1-amino methyl phthalazone-4 is acetylated. In pure
state no base could be obtained from the salts. The
reaction product of-the nitromethyl phthalazone with
zinc dust in the hydrogen current leads to the compound
(XI) which, according to its properties, represents the
indazole. There are 4 references, 2 of which are Soviet.
LSSOCIATION: Latviyskiy gosudarstvennyy universitet i Rizhskiy
meditsinskiy institut "" (Lat~lian- State University and
Riga Medical Institt-..~-"
SUBMITTEP: September 12, 1957
Card 2/19'

I
AUTHO-'-'S: Geyta, L. S., Vanag, G. Ya. SOY/79-28-lo-35/6o
TITLE: Compounds With Two Heminal Indandione Groups in the Molecule
(Soyedineniya a dvumya geminallnymi indandionovymi
gruppami v molekule) II.Condensation of 5,6-Dinitro
Acenaphthene Quinone With Inlandione-1,3(II. Kondensatsiya
5,6-dinitroatsenaftenkhinona s indandionom-1,3)
PERIODICAL: Zhurnal obshche khiriii, 1958, Vol 28, Nr lo,
pp 28ol - 2805 ~USSR)
ABSTRACT: In earlier papers the authors (Refs 1-6) showed that
many caxbonyl compounds easily condense with indandione-1,3,
so that, according to the conditions prevailinG in-
dandionylene derivatives of type (1) or diindandionyl
derivatives of type (11) may be isolated. The compounds
(I) easily affiliate another molecule indandione and
convert into the compounds (II); the latter again can
oplit off one molecLle indandione and convert again
into the compounds (I) (Scheme 1). Such reciprocal
conversions were realized with the condensation products
of indandione with benzaldehyde, nitrobenzaldehydes and
Card 1/3 acenaphthene quinono, whereas with phenanthrone quinone

Compounds With Two Heminal indandione Groups in the SO'1/79-28-lo-75/6o
Molecule."'II. Condensation of 5,6-Dinitpro Acenaphthene Quinone With
Indandione-1,3
and nitrophenanthrene quinone only compounds of the
type (II) viere obtained. Irf the prcaent paper the
condensation of the 5,6-dinitro acenaphthene quinone
with indandione-1,3 was carried out. If the condensation
takes place at a molar ratio of 1:1 in glacial acetic
acid the reaction goes into two directions and red
crystals of the 5,6-d4nitro-2-indandionyleneacenaphthenone-1
(III) as well as colorless crystals of 5,6-dinitro-2,2-
diindandionyl acenaphthenone-l(IV). The solubility of
the two products is almost the same so that a more
complete separation is not so easy, and only a
repeated boiling with chloroform, glacial acetic acid
and a more careful treatment with warm pyridine is
successful. It is known (Ref 7) that the indandione
nucleus without an activo hydrogren in thc- position 2
is easily subjected to cleavaCe by alkali liquor under
the formation. of carboxylic acid. Compound (III) eai3ily
converts to the unst-.ble dibromide (V) under the
Card 2/3 absorption of a- furthn-r molecule indandione (IV) and

Compounds With Two Heminal Indandione Groups in the SOY/79-28-10-35/6o
Molecule. II. Condensation of 5,6-Dinitro Acenaphthene Quinone With
Indandione-10
the absorption of one molecule bromine. Compound (IV)
easily is subjected to cyclization into the spiro
pyrane (VI) which on harder conditions with ammonia
and amines converts to the dJ.hydro pyridine (VII).
There are 7 references, 6 of which are Soviet.
ASSOCIATION: Institut organiolieskogo sinteza Akademii nauk Latviyskoy SSR
(Institute of OrGanic Synthesis,..* AS IAtViau SSR)
SUBMITTED: August 22, 1957
Card 3/3

AUTHORS: Ozol, ia.K. Zelmen,V.!$-'., "all, ~G-ia_ 3011/_19-26-11-40/55
TITLE. 2-Diphenyl-Acetyl-Indandione-1,3 (2-Difenilatsetilindandion-1,3)
PERIODICAL: Zhurnal obshchey khimii, 1958, Vol 26, Nr 11, PP 3083-3065 (6]3R)
ABSTRACT; Of late scientists became interested in the 2-subotituted indun(icne-
1,3-because of their phygiological activity. According to data in
publications some of them ahow an antibactorial, othors an in-
secticide activity. The 2-phenyl-indandione is an active preparation
against blood coagulation and is already used in medicine. Tne 2-di_
phenyl-acetyl-indandione-1,3 (I) is stillmore efficient. It differs
from other traditional blood anticoa6uiants (e.6. diocumarol,phenyl-
indandione) by the fact that already in smaller doses it causes a
considerable decrease of the prothrcmbin level of the blood. Be-
sides,it was found that the diphenyl-acetyl-indandicne is a valuable
means in fighting harmful rodent.
CO
C 6H4 _~ \CHCOCH(C 6H5)2 (1)
I'll CO/
Card 1/2 Compound (I) was synthesized by the condensation of the dimethyl

2-Dipbenyl-Acetyl-Indandione-1,3
'07/79-28-11-40/r,5
phthalate with diphenyl acetone;,It is separated from acetone in
good crystals that melt at 146- 70. The crystals are of priomatic
nature (Figure). The gcniometric data of the cryatals aro eiven in
the table.-There are 1 figure, 1 table, and 2 Soviet reference8.
ASSOCIATION. Institut khimii i Institut organicheskogo sinteza Arkademi'L nau?
Latviyskoy SSR (In3titute of Chemistry and Institute of Organic
Synthesis of the Academy of Sciences ILatviyskaya S3R)
SUBMITTED: October 30, 1957
Card 212

VANAGS, G.t Zelmene, V.; Krastina, Z.
:w- -
Halogenation of some 2 acylindandiones 1, 3. In Russian. p. 75.
IATVIIAS PSR ZINATNU AKADE?AIJA. VESTIS. RIUCA, LATM. Eo. 7, 1959
Monthly List of East F4ropean Accessions. (ELAI) LC, Vol. 9, no* 2,
Feb. 1960 Uncl.

GUDRINIYETSE, E.-[Gudriniece, E.] (Riga); IYEVINISH, A. (Ievins,A.A (Riga);
UIAQ-.G [Van2gs,G.l (Riga); XURGAN, D.
Research in the field of cyclic arylazo-,4-diketones. IV. Metallic
complexes of phenylazodimedons. Vestis Latv ak no.9:101-105 159.
(EEAI 9:10)
1. Akademiya nauk Latviyakoy SSR, Institut khimii.
(Aryl groups) (Ketones) (Dimenthylcyclohexanedione)
(Metals) (Phenyl group) (Azo compounds)
(Complex compounds) (Nickel) (Cobalt)
(Copper) (Silver)

- , - " ~ ... V , , :,: 71' AT ea cl, 2-
1 1 - .11;a- - - 1. ~

STRADINItyla. [Stradin89J.] (Riga); VANhG, G. [Vanags)G.) (Riga)
Polarographic behavior of 2-nitroWandlone-10s Veatis Latv ak
no.11:79-86 159. (EEAI 9111)
1, Akademiya nauk Latviyskoy SSR, Institut organicherkogo sinteza.
(Nitroindandione)
(Polarograph and polarography)

VANA09G, [Vanags,,G..] (Riga); DUMPIS, T. (Riga)
2-(Xethoxybenzyl)-indandione-lp3o Veatis Latv ak no,12;63-70 159,
(Em 91U)
1, Akademiya nauk Latviyakay SSFtq Institut organicheekogo, sinteza.
Undandione)
(Benzyl group)
(Methoxy group)

5 (3)
AUTHORS: Vanagg G. Ya., Gren, E. Ya., SOV/153-2-2-131/31
Tt-a-nreF7a-cH-,E. I.
TITLE: Polycyclic Heterocyclic Compounds (Mnogoyadernyye
geterotsiklicheakiya soyedineniya). I. 4-Phenyldibenzoylene
Pyridine (I- 4-fenil-dibenzoilenplridin)
PERIODICALs Izvestiya vysshikh uchebnykh zavedeniy. Khimiya i
khimicheskaya tekhnologiya, 1959, Vol 29 Nr 2t pp 210-214 (USSR)
ABSTRACT: Recently the authors proved (Ref 1) that 4-phenyl~2,3 (CO)t
6,5 (CO)-dibenzoylene pyridine (VII) develops when
benzalindandione-1,3 (II) is heated with ammonium acetate in
glacial acetic acid. The mechanism of thib reaction was
explained. It proved that under the conditions of this reaction
benzylindandione (11) partially decomposes in its primary
compounds; benzaldehyde and indandione-193 (I). The latter
immediately is added to the active ethylene linkage of the
benzalindandione and forms diindandionylphenyl methane (III)
(Ref 2). The compounds of the latter type easily split off a
water molecule from their enol forms (IV) and result in the

C
rd 1/3 corresponding pyranefi- (V). In these however the oxygen bridge
a is replaced by,nitragen: under the influence of ammonia. In this

Folycyclic Heterocyclic Compounds. I. 4-Pnenyldi- 307/153-2-2-13/31
benzoylene Pyridine
process they changed into the corresponding dihydropyridines
(VI) (Refs 3-8). It proved however that heminal
4iindandione compounds of the type (III) are immediately
changed into the corresponding 1,4-(or 3,4 ?)-dihydropyridines
(Ref 9) under the Influence of ammonium acetate. The
mechaniam of that change is not quite clear yet. These
dihydropyridines are transformed int6 pyridines if exposed to
the air (or quicker, if H 202)(see scheme). Since the method
given above is the quickest way for producing aryldibenzoylene
pyridines, the problem should be dealt with in detail, in
order to explain its scope of application. As expected,
o- and p-nitrobenzal indandiones produced the corresponding
nitrophenyl-dibenzoylene pyridines (VIII, IX) (Ref 2). In
contrast to further statements given in reference 2, the authors
succeeded in producing the corresponding dibenzoylene pyridines
by means of heating the arylidene Indandione which contained
a nucleophilic substitute. The reaction however takes place
much more slowly and the output is much lower. Anisal,
Card 2/3 salicylal, vanillal and veratral indandiones reacted positively

Polyoyclic Heterocyclic Compounds. SOT/153-2-2-13/31
I. 4-Phonyldibenzoylene Pyridine
in producing the substances X-XIII. All of the produced
phenyldibenzoylene pyridines are yellow or orange substances
with a very high (often over 3000) melting point, only the
ortho-derivatives are crystalline. Their chemical activity is
low. The rest of their properties is described. Since the
aoylates of the oxy compounds under discussion are yellow,
and their alkaline salts are red or red violet, one has to
draw the conclusion that during the salt production a
tautomeric change of tho oxy oompounds takes place. Finally
analogies of the recently publitthed article, reference 10, are
discussed. A simplification of the synthesis of the aryl-di-
benzoylene pyridines can be attained, if the arylidene
indandiones are not isolated. There are 13 references, 10 of
which are Soviet.
ASSOCIATIONt Latviyakiy gosudarstvennyy universitet; Kafedra organicheskoy
khimii (Latvian- State University, Chair of Organic Chemistry)
SUBMITTED: February 10, 1958
Card 3/3

I VANAG,, G.Ya.; STAMVICH, R.Yu.; ROMDAN, Tu.P.
Improvement of the method for producing hexenal. Med.proa. 13
no.9:27-28 S 159. (KM 13:1)
1. Inatitut organichesko 0 8i teza Akademii nauk Latviyakoy SSR.
OBARBITAL)

5 (3)
AUTHORS: Gudriniyetse, E, Yu., Iyevin'sh, A. F., SOT/79-29-3-44/61
'Lanag, G. Ya.
TITLE: Sulfonation 7A' P-Diketones (Sullfirovaniye P-diketanov).
IV- 5,5-Dimethyleyclohexanedidne-113-sulfo-2-acid and Its Salts
(M 5,5-Dimetiltaikloge-keandion.-1,3-oullfo-2-kislota i yeye
soli)
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 3, PP 959-963 (USSR)
ABSTRACT: Th,~ sulfonation' )f P-diketones with dioxane sulfotrioxide
(Refs 1,2 ) takes place easily, as well as with 98 '/a H2 so4in
the presence of acetic anhydride (Refs 3,4). In the work under
review the authors continued thi: sulfonation and their
attention was specially attracted by the salts of the above
acid (dimedon sulfo ac-W. Besides the acid, two series of
its salts were synthesized, with an equivalent of the metal (I)
and with two equivalents (II)
Card 113

Sulfonation of P-Diketonoo. IV. 5#5-Dimethyloyclo-
hexanedione-1,3-oulfo-2-acid and Its Salts
CH 3\ CH3
.C
H2 CH2
Oc CO
~C)
CHSO 3Me
(I)
BOY/79-29-3-44/61
CH H3
C
H2 C H2
Oc We I
( ~So -
so 3MeI
(II)
The acid is obtained in crystalline form. Dimedon is formed by
heating with hydrochloric acid. Ammonium-, sodium-9 magnesium-,
calcium-, strontium-, barium-, nickel-, and cobalt salts, with
an equivalent of the metal, were obtained by saturation of
the aqueous solution of dimedon sulfo acid with the correspon-
ding chloride. All metal salts, with the exception of nickel-
and cobalt salt, are obtainable in crystals and are soluble
in water. The aqueous solution of the salts with an equivalent
of the metal has an acid reaction. The dissolved dimedon sulfo
Card 2/3 acid yields Bulfa salts with organic bases (e.g. with aniline,

Sulfonation if P-Diketones. IV- 5,5-DimethYloYclo- SOV/79-29-3-44/61
hexanedione-1,3-sulfo-2-acid and Its Salto
pyridinegand quinoline). With the same ease it forms salts of
the enol form (II). These salts are obtained by neutralizing the
aqueous solution of the sulfo acid with carbonates or hydroxid-
es until the weakly acid or neutral reaction. The salts of
alkaline and alkaline-earth metals, as well as those of copper,
zinc, and manganese~ have an alkaline or neutral reaction in
aqueous solutions, depending on the properties of the cation.
The ammonium salt of the enol form could not be obtained. As
is the case with other sulfo acidsp the reaction of the
dimedon sulfo acid with S-benzylthiouronium chloride leads
to the benzylthiouron.'Lum salt (III). There are I table and
5 referencesq 3 of which are Soviet.
ASSOCIATION: Latviyskiy gosudarstvennyy universitet (Lat-vian State Universi-
ty)
SUBMITTED: January 16, 1958
Card 3/3

50) SO';/79-29-6-26/72
AUTHORS: Gudriniyetse, E., Vanag, G., Strakov, A., Neyland, 0.
TITLE: Sulforiation of A -Diketones (Sullfirovaniye ~ -diketonov).
VI. Derivatives of Indandione-1,3-f-~ulfonic-2-acid (VI.Proiz-
vodnjye indandion-1,3-sulifo-2-kieloty)
PERIOD1CAL; Zhurnal obshchey khimii, 1959, Vol 29, Nr 6,
Pp 1893 - 1897 (USSR)
ABSTRACT: There are no data available in publications regarding the
derivatives of the keto group of the sulfonic acids of the
ketones and aldehydes (Ref 1). Although the dioxime of the
indandione-1,3-sulfonic-2-aoid obtained from its dipotassium
salt and hydroxylamine hydrochloride in the presence of K 2C03
was described (Ref 2), the authors were not able to attain
the same results, neither with the disodium nor with the di-
potassium salt of this acid. On addition of alcohol the initial
product, and not the dioxime described, precipitated.
Card 1/3

Sulfonation of ~-Diketones. YI. Derivatives of Indandione- SOY/79-29-6-26/72
1,3-sulfonic-2-acid C----Ohle
C
1~
HSO3Me C so3Me 0 3Me
*0
NOH NH
(I) (II) (III)
The experiments under review indicated that the oxime M, is
readily formed on boiling of the sodium salt of the indandione-
1,3-sulfonic-2-acid in glacial acetic with hydroxylamine-hydro-
chloride, even without anhydrous sodium acetate. It is hardly
soluble in water and is transformed by bromination to give the
2,2-dibromo-indandione-1,3. The oxygen of the keto group of
the sodium salt of the acid mentioned is substituted by the
imino group with compound (II) being formed in the Me-NH 4* When
treating compound (II) with the alcoholic solution of sodium
hydroxide or sodium ethjlate compound (IV) (Me-Na) was formed,
the bipolar structure of uhich was confirmed by the ultraviolet
Card 2/3 absorption spectra. A number of derivatives of the indandione-
1,3-sulfonic-2-acid was thus synthesized (the oxime, semicarba-

Sulfonation of P-Diketones. VI. Derivatives of :,0V/79-29-6-26'72
Indandione-1,3-oulfonic-'e'-acid
zone, imine and phenyl-imine in the form of the sodium, ammonium
or aniline salts)., Bromination of the sodium salt of the oxime
of the above-mentioned acid and of the aiamonium salt of the
imine of tile same acid (V) yielded 2,2-dibromo-indandione-1,3.
Phosphorus pentachloride forms with the sodium salt of the acid
the 2-chloro-indandione-l,,3-sulfonic-2-acid-ohloride. Its bro-
mination result:3 in 2-cliloro-.2-bromo-indandione-1,3.',Vhi?n
boiling the sulfo-ohloride with alcohols 30 2 develops, which is
transformed into 2,2-dichloro-indandione-1,3. There are I figure
and 11 references, 6 of which are Soviet.
ASSOCIATIONs Latviyskiy gosudarstvennyy universitet (Latvian State University)
SUBMITTED: May 19, 1958
Card 3/3

50) SOV/20-125-3-2,2/63
AUTHORSt Vanags,,G. J., Academician AS Latviyakaya SSR, Dumpis, T. T.
TITLE: A New Method of Synthesizing 2-Aralkyl Indand-iones-1,3 (NovyY
sposob sinteza 2-aralkilindandionov-1,3)
PERIODICAL: Doklady Akademii nauk SSSR, 1959, Vol 125, Nr 3, PP 549-552
(USSR)
ABSTRACT; An efficient anticoagulant of blood: 2-phenyl-indandione-1,3
(Refs 1-6), known as 11-fenilin" in the USSR, is at present es-
pecially noted among the indandione-1,3 derivatives, since it
has various advantages compared with dicumarine. It is possible
that other derivatives, e.g. amino derivatives of "fenilin" may
be used in practice as well (Refs 7-9)- In this connection the
next analogue of "fenilin", i.e. the 2-benzyl-indandione-1,3
(IV Ar - C6H5) is interesting as well. Only a derivative (II)
of the latter is known (Refs 10,11). The production of the
indandione-1,3 which was tried by means of 3 methods (Refs 13,
10,11) failed. The general method of production of 2-substitut-
ed indandiones is based upon the K'_eisL~2 (Klyayzen) condensa-
Card 1/3 tion of dialkyl phthalate with esters of the monocarboxylic

A New Method of Synthesizing 2-Aralkyl Indandiones-1,3 SOY/20-125-3-23/63
acids (Ref 14). neither the physical properties nor the
yields of the 2-benzyl indandione-193 thus produced are given
in reference 11, the authors worked out a new methods the sub-
stances mentioned in-the title are produced (IV) by the hydra-
tion of the 2-arylidene indandiones-1-0 (III). Aromatic alde-
hydes may be easily condensed with-indandipne-1,3 and form
2-arylidene indandiones-1.0 (III). Further transformationa of
the 2-ben-z&l-indandione-1,3 (III Ar . C6H5) under the action of
sodium hydrogen sulfite (V) by-the Wojack reaction (Refs 11, VI)
are given. Table I shows the seven aralkyl indandiones produced
by the hydrogenation of the arylidene indandiones with sodium
hydrogen sulfite. Dialkyl amino arylidene indandiones do not
form bisulfite compounds, therefore the yields of the dialky!
amino benzyl indandiones are higher. Good yields were obtained
by the-hydrogenAtion of the benzal indandione by hydrogen in-the
presence of skeleton nickel. A special communication on this
topic follows. An experimental part gives the usual data. There
are 1 table and 16 references, 6 of which are Soviet,
Card 2/3

A New Method of Synthesizing 2-Aralkyl Indandiones-10
SOV/20-125-3-23/63
ASSOCIATION: Institut organicheskogo sinteza Akademii nauk Latviyakoy SSR
(Institute of Organic Synthesis of the Academy of Sciences
of the Latviyskaya SSR)
SUBMITTEDt - December 12, 1958
Card 3/3

5 (3)
AUTHORS:
Vanag,. G. Ya., Member of the MadeW SOV/20-125-4-30/74
-K-c-aZ,em`y---oT-9`ciences of the LatvSSH, Lukevit3, E. Ya.
TITLEt Interaction Between 2-Bromo-2-Phenylindandione-1,3 and
Grignard Reagents (Vzaimodeystviye 2-brom-2-fenilindandiona-1,3
a reagentalhi Griri.tyara)
PERIODICALt Doklady Akademii nauk SSSR, 1959, Vol 125, Nr 4, pp 801-802
(USSR)
ABSTRACT: It was assumed (Ref 2) that in-conneotion with the interaction
between 2,4-dibromo-2,4-dimethyl pentanone-3 and methyl
magnesium iodide (2,2,4-trimethyl pentanone,3is formed) (Ref 1)
a bromine atom in a-position to the carbonyl group is replaced
by MgJ. As later explained, in this reaction a derivative of
the enol-form of ketone forms (Refs 3, 4). Also in the case
of the halogen-substituted P-diketones halogen was found to be
replaced by hydrogen under the action of the Grignard reagent
(Ref 5). In the latter case a reaction scheme (Ref 6) was
suggested (see scheme). If the a-halogen ketone is considerably
enolized the halogen is not exchanged for hydrogen, but
hydrogen of the enol group reacts with the Grignard reagent
Card 1/3 (e.g. see scheme; Ref 7). In the case of an interaction of the

1P
Interaction Between 2-Bromo-2-Phenylindandione-1,3 SOV/20-125-4-30/74
and Grignard Reagents
substance mentioned first in the title.(II) with trimethyl
silyl methyl magnesium chloride the authors observed the
formation of 2-phenylindandione-1,3 (III). In order to be
able to check the scheme of reference 6 the authors carried
out the reaction of (II) with ethyl magnesium iodide. When
equivalent amounte of the reagents were taken it was possible
to isolate (III) from the reaction mass. In the case of an
excess quantity of ethyl magnesium iodide the second carbonyl
group reacted also and 3-ethyl-2-phenylindanol-3-on-1 (IV.) was
obtained. The -latter was transformed into 3-ethyl-2-phenyl-
indenone-1 (V) (Ref 8). In connection with the investigation
of the ~-Grignard reagent.it was found that phenol magnesium
bromide and iodide give a bluish luminescence in the case of
an oxidation in the air. The luminescence is soon over in order
to occur again under friction. The luminescende of iodide is
less intensive than that of bromide. In the case of methyl
magnesium iodide and ethyl magnesium bromide no luminescence
was observed. The usual data are given in the experimental part.
Card 2/3 There are 10 references, 3 of which are Soviet.

Interaction Between 2-Bromo-2-Phenylitidandione-1,3 SOV/20-125-4-30/74
and Grignard Reagents
ASSOCIATIOIN Institut organioheakogo sinteza Akademii nauk Latviyskoy SSR
(Institute of Organic Syntheais of the Academy of Sciences
of the Latviya S3R)
SUBMITTEDt November 12, 1958
Card 3/3

66419
AUTHORS: Gudriniyetseq E. Yuoq Lyf~nagq Go Yao.9 SOV120-128-6-23163
Academiciang AS LatYSSR, Sakharg Lo Yu*
TITLE: Condensation of the Sodium Salt of Ethyl Raters of Indandione-
10-carboxylio-2-acid. With Diazotized Nitroanilines
PERIODICAL: Doklady kkademii nauk SSSR9 1959, Vol 1289 Nr 6, pp 1182 - 1184
(USSR)
ABSTRACT: There are no publication data on the interaction of Indandione-
193-derivatives with aryl-azo compounda. If the interaction re-
action of the latter with eaters of cyclohexanone-carboxylic
acids is carried out in a neutral or weakly acid medium, cyclane-
dion-aryl hydrazones are formed (Refs 10-12). In a strongly al-
kaline medium, the*ring is disrupted, and aryl hydrazones of
keto-dicarboxylic acids are formed (Refs 12-16). The authors in-
vestigated the products of the condensation reaction of the o-,
m-9 and p-nitroanilines mentioned in the title with the sodium
salt also mentioned there. Apparently, the reaction proceeds
with a displacement of the reaction center (Ref 18), not accord-
ing to Dimroth's mechaniam (Refs 19,20). The'aryl-azo compounds
(I) obtained by the authors are yellow, insoluble in water, but
Card 113 well soluble in methanolq ethanol, acetone, ether, glacial 41

66419
Condensation of the Sodium Salt of Ethyl Eaters of BOT/20-128-6-23/63
Indandione-1,3-carboxylic-2-acid With Diazotized
Nitrodnilines
acetic acidg and dioxane. On heating an alcoholic solutiong the
corresponding 2-(nitrophenyl)-hydrazone-indandionee-1.3 (II, see
Diagram) are formed. (II) were also obtained in an alkaline
medium (pH- 8-9). The ethyl eater of the 2-(p-nitrophenyl)-azo-
indandione-193-carboxylic-2-acid (Ia) crystallizes from diluted
ethanol with I molecule of water, and yields a monoxime, On
boiling the alcoholic eolutiong 2-(p-nitrophenyl)-hydrazone-in-
dandione-193 (II) is formed. The ethyl eater of the acid (1a)
dissolves in alkalis while the color turns into red. At the same
time, the indandione ring is hydrolytically split, and the sodium
salt of the ethyl eater of the p-nitrophenyl hydrazone of o-6-car-
boxy-benzoyl-glyoxalic acid is formed. On acidification of the
solution, this acid (III) is also separated in the form of a
yellow precipitation., The red diaodium salt (IV) of the acid (III)
waj isolated by heating the azo eater (Ia) with sodium ethylate
in ethanol. Besideaq the well water-soluble salts of the acid
(III) were produced: monoammonium-, di-diethylamine-9 and di-
piperidine salts. The acid (III) is resistant to hydrolysis, and
Card 2/3 splits off the ethoxyl group Qnly after boiling in an acetic /

66419
Condensation of tho Sodium Salt of Ethyl Esters of SOV/20-128-6-23/63
Indandione-lt3-carboxylic-2-acid With Diazotized
Nitroanilines
oulphuric-acid mixture for 5 hours. Here, the p-nitrophenyl
hydrazone of the o-carboxyphenyl glyoxal (T) is formed. Thus,
the authors succeeded for the first time in producing derivatives
of cyclic P-diketones. There are 20 references, 5 of which are
Soviet.
ASSOCILTION: Rizhakiy politekhnicheskiy institut (Riga Polytechnic Institute)
SUENITTED: June 29, 1959
Card 3/3