Investigations in the area of functionally substituted azines. 5.* Reactions of azines with nucleophiles and hydrogen chloride

It was shown that oxazolopyrimidinium and sym-triazinium chlorides give N₍₃₎-(2-Y-ethyl)-substituted azines with nucleophiles. Oxazolo-sym-triazine also reacts analogously, being converted by hydrogen chloride to the N₍₃₎-(2-chloroethyl) derivative.Armenian Agricultural Academy, Yerevan, 375009. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1417–1420, October, 1996. Original article submitted April 15, 1996.     

New method for synthesis of 3-pyrrolin-2-one derivatives

We propose a method for synthesis of derivatives of pyrrolinone by reaction of the methyl ester of 3-substituted 2-oxo-3-pentonoic acid with primary amines or acetylhydrazine.Institute of Organic Chemistry, National Academy of Sciences of the Armenian Republic, Yerevan 375094. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1345–1350, October, 1994. Original article submitted July 4, 1994.     

Investigation of the stereodirection of the Ritter reaction. Crystaline and molecular structures of N-(2-phenethyl)-2,5-dimethyl-4-phenylpiperid-4-ol and N-(2-phenethyl)-2,5-dimethyl-4-phenyl-4-acetamidopiperidine

The stereodirection of the Ritter reaction of N-(2-phenethyl)-2,5-dimethyl-4-phenylpiperid-4-ol to the corresponding amide has been studied. X-ray analysis has shown that the reaction occurs with retention of the configuration about atom C₄ of the piperidine ring.A. L. Mndzhoyan Institute of Fine Organic Chemistry, Armenian Academy of Sciences, Yerevan 375014. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1384–1390, October 1994. Original article submitted September 28, 1994.     

Investigation of the stereodirection of the Ritter reaction. Crystalline and molecular structure of N-(2-phenethyl)-4-methylpiperid-4-ol and N-(2-phenethyl)-4-methyl-4-acetamido-piperidine

The stereodirection of the Ritter reaction of N-(2-phenethyl)-4-methylpiperid-4-ol to the corresponding amide has been studied. X-ray analysis has shown that the reaction occurs with retention of the configuration about atom C₄ of the piperidine ring. Attempts are made to explain the stereodirection of the direction.A. L. Mndzhoyan Institute of Fine Organic Chemistry, Armenian Academy of Sciences, Yerevan 375014. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1391–1396, October, 1994. Original article submitted September 28, 1994.     

Mass spectrometric identification of ring-chain tautomers of 4-cyano-3-pyrazolidones in the gas phase

Analysis of the electron impact mass spectra of a series of 4-cyano-3-pyrazolidones, which manifest ring-chain tautomerism in polar solvents, showed that these compounds also exist in the gas phase as a mixture of tautomers, which undergo characteristic fragmentation. The quantitative tautomer ratio in this series is a function of electronic and steric substituent effects. The fragmentation pathways for each of the tautomers were determined using high-resolution mass spectrometry.M. V. Lomonosov Moscow State University, 119899 Moscow. Yerevan State University, 375025 Yerevan. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp 1525–1530, November, 1995 Original article submitted November 1, 1995.     

Synthesis and transformations of 6-amino-3,5-dicyano-4ethylpyridine-2(1H)-thione

The condensation of propionaldehyde with cyanothioacetamide gives 6-amino-3,5-dicyano-4-ethylpyridine-2(1H)-thione, which was used to obtain substituted 2-alkylthiopyridines, 2-ethylthio-6- ethylaminopyridine, and pyrazolo[3,4-b]pyridine.T. G. Shevchenko Lugansk State Pedagogical Institute, 348011 Lugansk. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Science, 117913 Moscow. Translated from Khimiya Geterotsklicheskikh Soedinenii, No. 8, pp. 1094–1098, August, 1996. Original article submitted March 4, 1996; revision submitted July 1, 1996.     

Synthesis of substituted 2-alkyl(aryl)thio-3-cyanopyridines and 3-aminothieno[2,3-b]pyridines

The alkylation of 6-methyl-4-methoxymethyl-3-cyano-2-(1H)pyridinethione by halogen derivatives in the presence of KOH proceeds regioselectively with the formation of S-alkyl derivatives. By cathodic electrolysis of the thiols in the presence of 6-methyl-4-methoxymethyl-2-chloro-3-cyanopyridine, 2-arylthiopyridines are obtained. By Thorpe-Ziegler cyclization of 2-alkylthiopyridines having an ctive methylene group, 2-aminothieno[2,3-b]pyridines have been synthesized.Kuban State Technological University, Krasnodar, 350072. N. D. Zelinskii Institute of Organic Chemistry, Moscow 117913. Southern Branch of Association Rosvuznauka, Krasnodar, 350072. Translated from Khimiya Geterotsiklicheskikh Soedinenii, NO. 10, pp. 1432–1437, October, 1996. Original article submitted April 2, 1996; revision submitted August 20, 1996.     

2a,4a-Diazacyclopenta[c,d]Azulenes

A method of preparing 5-aryl-1,2-pentaniethyleneimidazoles from O-methylcaprolactim and -aminoacetophenone hydrochlorides is described. It is shown that 1, 2-tri-, -tetra-, and -pentamethyleneirrüdazoles and phenacyl bromide give the corresponding quaternary imidazolium salts, cyclization of which in the presence of base gives the previously unknown 5,6, 78-tetrahydro-2a, 4a-diazacyclopenta(c,dJazulenes (IVa-i).T. G. Shevchenko National Unkiversity, Kiev 254017. T. G. Shevchenko Educational Institute, Chernigov 250037. Translated from Khimiya Geterotskilicheskikh Soedinenii, No. 8, pp. 1072–1077, August, 1996. Original article submitted February 27, 1996; revision submitted June 27, 1996.     

4-Hydroxy-2-quinolones. 31. 3-Amino-ir-2-oxo-4-hydroxyquinolines and their acyl derivatives

Abstarct An alternative method has been developed for preparing and studying the antioxidant activity of 3-acylamino-2-oxo-4-hydroxyquinolones. Results are presented from an investigation of the antithyroid and antimicrobial action of the intermediate 2-oxo-3-(1 pyridinio)quinotin-4-olates and the 3-amino-2-oxo-4-hydroxyquinolines.For communication 30, see [1].Ukrainian Pharmaceutical Academy, Khar'kov 310002. Translated from Khimiya Geterotsklicheskikh Soedinenii, No. 8, pp. 1113–1123, August, 1996. Original article submitted June 10, 1996.     

Synthesis of 1,2,4-triazolo[4,3-c]-, tetrazolo[1,5-c]-, and 1,2,4-triazino[5,6-c]pyrano[4'3':4,5]pyrrolo-[3,2-e]pyrimidine derivatives

4-Hydrazinopyrano[4',3':4,5]pyrrolo[2,3-d]pyrimidines served as precursors in the synthesis of new heterocyclic systems, namely, 1,2,4-triazolo[4,3-c]-, tetrazolo[1,5-c]-, and 1,2,4-triazino[5,6-c] pyrano[4',3':4,5]-pyrrolo[3,2-e]pyrimidines.A. L. Mndzhoyan Institute of Fine Organic Chemistry, National Academy of Sciences of the Republic of Armenia, 375014 Yerevan. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 700-703, May, 1995. Original article submitted January 10, 1995; revision submitted April 20, 1995.     

2-[2-(Dimethylamino)vinyl]-6-pentafluorophenyl-4-phenylpyrylium perchlorate and its hydrolysis products: Synthesis and isomerism

2-(2-(Dimethylamino)vinyll-6 pentafluorophenyl-4-phenylpyryliunt perchlorate has been synthesized and it was shown that it is readily converted into 2-fornrylntethylene-6-pentafluorophenyl-4-phenyl-2H-pyran on chromatography on alkaline Al₂O₃. The stereoisornerism of the synthesized compounds has been studied by PMR spectroscopy.Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences (SO RAN) Novosibirsk 630090. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1188–1194, September, 1996. Original article submitted March 29, 1996.     

4-Hydroxy-2-quinolones. 30 Alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline

A study has been made of the alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline by alkyl halides in the presence of inorganic bases. New methods for the synthesis of 1-substituted 2-oxo-3-carbethoxy-4-ihydroxyquinolines are examined.For communication 29, see [1].Ukrainian Pharmaceutical Academy, Khar'kov 310002. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1104–1112, August, 1996. Original article submitted June 10, 1996.     

Synthesis and conversions of 5-(3,5-6-trichloro-1,4-benzoquinon-2-yl)-2-isopropylidenehydrazinothiazole and 2-isopropylidenazinothiazolines

When 2,5-dihydroxy-3,4,6,7-tetrachloro-2,3-dihydrobenzo[b]furan interacts in acetone with thiosemicarbazide or its 4-methyl or 4-phenyl derivative, the respective products are 5-(2,5-dihydroxy-3,4,6-trichlorophenyl)-2-(isopropylidenehydrazino)thiazole and -3-R-2-(isopropylidenazino)thiazolines, respectively. It has been shown that hydrolysis of these compounds forms 3-amino-5-(2,5-dihydroxy-3,4,6-trichlorophenyl)-2-imino(or 2-R-imino)thiazolines. These products of hydrolysis and their predecessors are oxidized to the corresponding 2-hetaryl-substituted 3,5,6-trichloro-1,4-benzoquinones.Riga Technical University, Riga, LV-1048. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1424–1431, October, 1996. Original article submitted July 1, 1996.     

Reaction of 2-allyloxy(thio)-4-methylquinolines with halogens

It was established that the halogenation of 2-allyloxy(thio)-4-methylquinolines leads to the formation of 3halogenomethyl-2, 3-dihydrooxazolo(thiazolo)[3, 2-a]quinolinium halides.Chelyabinsk State University, Chelyabinsk 454136. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1252–1254, September, 1996. Original article submitted July 7, 1996.     

Synthesis of n2-guanylcarboxylic acids

A novel method has been developed for synthesizing N²-guanylcarboxylic acids by reaction of 2-chloro-7-benzyl-hypoxanthine with amino acids and debenzylation of the 7-benzyl-N²-guanylcarboxylic add products by means of palladium catalyzed hydrogenation.Center for the Chemistry of Medicinal Compounds. All-Russian Chemico-Pharmaceutical Science Research Institute, Moscow 119815. State Institute for Blood Substitutes and Medicinal Preparations, Moscow 109044. Zaporozh'e State Medicinal Institute, Zaporozh'e 330074. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 395–398, March, 1996. Original article submitted January 17, 1996.     

Synthesis of dialkyltetrahydrobenz[f]iso-indoline,dialkyl-4-δ′-cyclohexenylbenz[f]iso-indoline,and dimethyl-4-alkenylnaphth[f]iso-indolive salts through base-catalyzed intramolecular cyclization of quaternary ammonium salts

Dialkylpropargyl(3-,-cyclohexenylpropargyl)amrnonium salts are cyclized in the presence of a base catalyst to give dialkyltetrahydrobenzlfliso-indoline salts in high yields. When the 3--cyclohexenylpropargyl and 3 phenylpropargyl groups are both present in the ammonium salt molecule, cyclization proceeds in more than one direction. Salts which contain both the 3-a-naphthylpropargyl and 3-alkenylpropargyl groups are also cyclized in two possible ways.Institute of Organic Chemistry, Republican Academy of Sciences, Armenia, Yerevan. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 328–332, March, 1996. Original article submitted September 30, 1995.     

Reaction of 2-Iminobenzothiazolines with propylene oxide

The reaction of 2-iminobenzothiazolines with propylene oxide in methanol involves splitting of the thiazoline ring and formation of derivatives of o-aminothiophenol, urea, and oxazolidinone. It is shown that diaLkylaminobenzothiazoles, in contrast to their imino isomers, do not react with oxiranes.Phytochemistry Institute, Academy of Sciences of Uzbekistan Republic, Tashkent 700170. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1279–1283, September, 1996. Original article submitted July 11, 1996.     

Reaction of 4,5-dihydroxy-2-imidazolidinones with arylsulfinic acids. Synthesis of 4-arylsulfonyl-2-imidazolinones

The reaction of 4,5-dihydroxy-2-imidazolidinones with arylsulfinic acids in water upon heating leads to 4-arylsulfonyl-2-imidazolinones. The formation of such compounds was found to proceed through the loss of a water molecule or sulfinic acid from intermediate 4-hydroxy-5-arylsulfonyl-2-imidazlidinones and 4,5-dihydroxy-2-imidazolidinones. 4-Arylsulfonyl-2-imidazolinones are also formed upon heating glyoxal, urea, and arylsulfinic acids in water.M. V. Lomonosov Moscow State Fine Chemical Technology Institute, 117571 Moscow. Translated from Khimiya Geserotsiklicheskikh Soedinenii, No. 10, pp. 1337–1342, October, 1996. Original article submitted July 17, 1996.     

Synthesis and properties of furan derivatives. 5. Synthesis of 2-substituted benzoxazoles containing furan fragments

The condensation of imidates and imidate hydrochlorides of furan acids with o-aminophenols gives furyl derivatives of 2-substituted benzoxazoles. Such compounds are also formed in the reaction of furan acids with o-aminophenol in the presence of boric acid.Communication 4, see [1].I. M. Gubkin State Petroleum and Gas Academy, 117917 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 896–901, July, 1996. Original article submitted April 16, 1996.     

Synthesis,chemical properties,and biological activity of 2-Amino-4-oxazolinones and their tautomeric 2-Amino-4-oxazolidones (Review)

Data on the synthesis and chemical and pharmacological characteristics of 2-amino-4-oxazolinones and 2-inzino-4-oxazolidones are reviewed.Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, Perm. Translated from Khimiya Geterotsklicheskikh Soedinenii, No. 8, pp. 1011–1025, August, 1996. Original article submitted August 16, 1995.