Chemistry of Heterocyclic Compounds (Khimiya Geterotsiklicheskikh Soedinenii) publishes articles, short communications, reviews and minireviews on the synthesis, structure, reactivity and biological activity of heterocyclic compounds including natural products. The journal covers investigations in heterocyclic chemistry taking place in scientific centers all over the world. CHEMISTRY OF HETEROCYCLIC COMPOUNDS is a translation of the journal Khimiya Geterotsiklicheskikh Soedinenii, which is issued by the Latvian Institute of organic synthesis. Editor-in-Chief: D. Volochnyuk Deputy Editors: P. Arsenyan, S. Ryabukhin Managing Editor: M. Teus Production Editors: N. Zhuk, A. Amoliņš Production Editor of the English Issue: N. Vereteņņikova Advisory Board: O. N. Chupakhin, G. Duburs, I. Kalvinsh, V. G. Kartsev, M. Makosza, V. I. Minkin, H. van der Plas, A. F. Pozharskii, A. A. Tolmachev, B. A. Trofimov, R. Valters, A. V. Varlamov Editorial Board: V. T. Abaev, A. V. Aksenov, N. A. Bumagin, V. A. Chebanov, S. M. Desenko, V. V. Dotsenko, L. L. Fershtat, V. Gevorgyan, B. Gnanaprakasam, O. O. Grygorenko, A. V. Gulevskaya, A. Gutnov, R. Jasiński, A. Kornienko, M. A. Kuznetsov, T. Opatz, V. A. Ostrovskii, A. E. Shchekotikhin, A. B. Sheremetev, Yu. G. Shermolovych, V. Z. Shirinian, V. Ya. Sosnovskikh, I. V. Trushkov, M. Turks, E. N. Ulomsky, A. V. Vasilyev, A. N. Vereshchagin, L. G. Voskressensky
The published data on the participation of cyanamides in heterodiene synthesis as dienophophiles were organized and generalized. How to Cite Nekrasov, D. D. Chem. Heterocycl. Compd. 1994, 30, 997. [Khim. Geterotsikl. Soedin. 1994, 1155.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171152
Copyright (c) 2026 Chemistry of Heterocyclic Compounds
Compounds of the thiophene series, accompanying aromatic hydrocarbons in technical mixtures: Complexes with organic solvents
The data available in the literature on the complex formation of thiophene, its homologs, and benzannelated thiophenes with organic solvents have been reviewed. How to Cite Zaretskii, M. I. Chem. Heterocycl. Compd. 1994, 30, 1004. [Khim. Geterotsikl. Soedin. 1994, 1163.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171153
Intramolecular cyclization of N-(4-aryl-5-pyrazolyl)formamidines
How to Cite Bogza, S. L.; Nikolyukin, Yu. A.; Dulenko, V. I. Chem. Heterocycl. Compd. 1994, 30, 1120. [Khim. Geterotsikl. Soedin. 1994, 1290.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171178
Reactions of polyhalopyridines. 9. Perfluoroalkylation of 2,3,5,6-tetrafluoro-4-mercaptopyridine with compounds of xenon containing fluorine
How to Cite Sipyagin, A. M.; Efremov, I. V.; Pomytkin, I. A.; Kashtanov, S. A.; Aleinikov, N. N. Chem. Heterocycl. Compd. 1994, 30, 1121. [Khim. Geterotsikl. Soedin. 1994, 1291.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171179
Arenesulfenylation of 1,3-azoles with arenesulfenyl chlorides
How to Cite Tolmachev, A. A.; Yurchenko, A. A.; Man'ko, V. A.; Merkulov, A. S.; Pinchuk, A. M. Chem. Heterocycl. Compd. 1994, 30, 1123. [Khim. Geterotsikl. Soedin. 1994, 1292.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171180
Molecular structure of 1-phenyl-2-chloro-3-(meta-nitrophenyl)-2,3-epoxypropanone
X-ray analysis was used to determined the structure of 1-phenyl-2-chloro-3-(m-nitrophenyl)-2,3-epoxypropanone, obtained by reacting phenacyl dihydrochloride with metanitrobenzaldehyde under Darzen's reaction conditions. The bulky m-nitrophenyl and benzoyl substituents were located in the trans position relative to the chloroepoxide fragment, which was found to stabilize when the m-nitrophenyl substituent was introduced. How to Cite Litvinov, I. A.; Mamedov, V. A.; Kataeva, O. N. Chem. Heterocycl. Compd. 1994, 30, 1012. [Khim. Geterotsikl. Soedin. 1994, 1172.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171154
2-benzopyrylium salts. 45. Interaction of 2-benzopyrylium salts and their monocyclic analogs with imines of ketones
It was shown that ketonimines, which can have imine--enamine tautomerism, react with pyrylium salts in the enamined form. In such reactions, the 2-benzopyrylium salts are transformed into unsaturated ketones, and their monocyclic analogs are transformed into either quinolizinium salts or pyridinium salts depending on the structure of the initial imine. How to Cite Tosunyan, D. É.; Verin, S. V.; Kuznetsov, E. V. Chem. Heterocycl. Compd. 1994, 30, 0151. [Khim. Geterotsikl. Soedin. 1994, 1176.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171155
Pyrylocyanines. 33. Pyrylocarbocyanines with bridge groups in the chromophore
Salts of 4,4-tetra-, penta-, and hexamethylene-bis-(2,6-diphenylpyrylium) and -thiopyrylium were synthesized and used as the basis for producing trimethylcyanines with ethylene, tri- and tetramethylene bridge groups in the chromophore. Factors influencing the color of these dyes were analyzed. The bis-pyrylium salts were converted to derivatives of pyridine, N-methyl- and N-phenylpyridinium. The structure of the compounds obtained was confirmed by the data of electron spectroscopy and PMR spectroscopy. How to Cite Kudinova, M. A.; Maiboroda, E. I.; Slominskii, Yu. L.; Tolmachev, A. I. Chem. Heterocycl. Compd. 1994, 30, 1024. [Khim. Geterotsikl. Soedin. 1994, 1186.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171156
Synthesis of some new derivatives of dithiene- and oxathienecarboxylic acids
Substituted anilides of 1,4-dithiene- and oxathienecarboxylic acids were synthesized. It was shown that the reaction of 3-phenyl-1,4-dithi-2-ene-2-carboxyl chloride with 2-aminopyridines, depending on the base used and the reaction conditions, leads to the formation of N-[3′-phenyl-2′-(1′,4′-dithi-2′-en)ylcarbonyl]2-aminopyridine and/or N,N′-bis[3-phenyl-2-(1,4-dithi-2-en)-ylcarbonyl]pyridonimine. The data of IR, UV, and PMR spectroscopy were used to confirm the structure of the synthesized compounds. How to Cite Mamedov, V. A.; Sibgatullina, F. G.; Gubskaya, V. P.; Gainullin, R. M.; Shagidullin, R. R.; Il'yasov, A. V. Chem. Heterocycl. Compd. 1994, 30, 1029. [Khim. Geterotsikl. Soedin. 1994, 1191.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171157
Pyrroloindoles. 16. Some electrophilic substitution reactions of 2,7-dicarbethoxy-1H,6H-pyrrolo[2,3-e]indoles
Electrophilic substitutions of 2,7-dicarbethoy-1H,6H-pyrrolo[2,3-e]indole (Friedel‒Crafts acylation, nitration, bromination) take place both at position 3 of the indole ring and at positions 5 and 8 in the benzene ring. How to Cite Lomadze, N. S.; Chikvaidze, I. Sh.; Targamadze, N. L.; Kurkovskaya, L. N.; Samsoniya, Sh. A.; Suvorov, N. N. Chem. Heterocycl. Compd. 1994, 30, 1034. [Khim. Geterotsikl. Soedin. 1994, 1197.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171158
It has been shown that Friedel‒Crafts p-nitrobenzoylation of 2,2′-dicarbethoxybis(5-indoyl)methane occurs at the bridging group. From the products of p-nitrobenzoylation of 2-carbethoxy-5-methylindole, 2-carbethoxy-5-hydroxy-indole and 2,7-dicarbethoxy-1H,6H-pyrrolo[2,3-e]indole there were obtained corresponding amines and an oxime. How to Cite Samsoniya, Sh. A.; Chikvaidze, I. Sh.; Gogrichiani, É. O.; Lomadze, N. Sh.; Targamadze, N. L. Chem. Heterocycl. Compd. 1994, 30, 1039. [Khim. Geterotsikl. Soedin. 1994, 1202.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171159
Synthesis of mono- and disubstituted tetra(tert-butyl)porphyrazines
Bromination of tetra(tert-butyl)porphyrazine by N-bromosuccinimide in chloroform results in the formation of mono- and dibromides, substitution for the bromine atoms of which produced the corresponding cyano, phenoxy, phenylthio, styryl, phenylethynyl and piperidino derivatives. From the monobromide and 2,2-bis(p-hydroxyphenyl)propane, the dimeric porphyrazine 2,2-bis[p-tetra(tert-butyl)porphyrazyloxyphenyl]propane was similarly obtained. How to Cite Makarova, E. A.; Kopranenkov, V. N.; Shevtsov, V. K.; Luk'yanets, E. A. Chem. Heterocycl. Compd. 1994, 30, 1043. [Khim. Geterotsikl. Soedin. 1994, 1206.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171160
Recyclization of spiro[3a-hydroxypiperidin-4,2′-oxiranes] in basic medium
It is shown that heating spiro[3a-hydroxypiperidin-4,2′-oxiranes] in aqueous base gives rearrangement into derivatives of 3,4-epoxypiperidines. The structures of the latter were confirmed by spectral data and by chemical informations. How to Cite Zvonok, A. M.; Okaev, E. B. Chem. Heterocycl. Compd. 1994, 30, 1049. [Khim. Geterotsikl. Soedin. 1994, 1213.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171161
Synthesis of spirocyclic 1,3-dioxolan-4-ones from α-hydroxyamides
It is shown that α,β-dihydroxypiperidine-4-carboxyamides in reaction with formaldehyde in concentrated sulfuric acid is converted to the corresponding 1,3-dioxolan-4-ones. How to Cite Lakhvich, F. F.; Stanishevskii, L. S. Chem. Heterocycl. Compd. 1994, 30, 1052. [Khim. Geterotsikl. Soedin. 1994, 1216.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171162
Stereochemistry of hydrocyanation of 3-hydroxy-4-alkyliminopiperidines
We have studied the stereochemistry of hydrocyannation of 3-hydroxy-4-alkyliminopiperidines. We have developed preparative synthesis methods for stereoisomeric 4-alkylamino-3e-hydroxy-1,3a-dimethyl-6e-(4-chlorophenyl)piperidines. How to Cite Lakhvich, F. F.; Khripach, N. B.; Stanishevskii, L. S. Chem. Heterocycl. Compd. 1994, 30, 1055. [Khim. Geterotsikl. Soedin. 1994, 1219.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171163
Reactions of 4-ethoxycarbonylbenzo[c]pyrylium with ammonia and primary amines
We have studied the reactions of 4-ethoxycarbonylbenzo[c]pyrylium perchlorates with ammonia and primary amines. We have obtained previously unknown derivatives of isoquinoline and 1-naphthylamine. How to Cite Bogza, S. L.; Zubritskii, M. Yu.; Dulenko, V. I. Chem. Heterocycl. Compd. 1994, 30, 1058. [Khim. Geterotsikl. Soedin. 1994, 1222.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171164
Alkylation of 2-, 4-, and 8-trialkylsiloxyquinolines by methyl iodide
Trimethyl- and triethylsilyl ethers of 2-, 4-, and 8-hydroxyquinolines have been prepared. The alkylation of these siloxyquinolines by methyl iodide has been studied. In the case of 4-trimethylsiloxyquinoldine, it has been established that both N- and O-alkylation products are formed. How to Cite Lukevits, É.; Segal, I.; Birgele, I.; Zablotskaya, A. Chem. Heterocycl. Compd. 1994, 30, 1061. [Khim. Geterotsikl. Soedin. 1994, 1225.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171165
Quaternization of 1H-imidazo[4,5-b]pyridine and 4-methyl-4H-imidazo[4,5-b]pyridine
Unsubstituted imidazo[4,5-b]pyridine adds methyl iodide to the pyridine N atom. Treatment of the resulting iodide with base forms 4-methyl-4H-imidazo[4,5-b]pyridine. This nucleophile can readily add methyl iodide to form only one salt, 1,4-dimethylimidazo[4,5-b]pyridinium iodide. How to Cite Yutilov, Yu. M.; Ignatenko, A. G. Chem. Heterocycl. Compd. 1994, 30, 1067. [Khim. Geterotsikl. Soedin. 1994, 1232.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171166
Amidoalkylation of mono- and dimercaptopyrimidines
Reaction of 2- and 4-mercapto- and 2,4-dimercaptopyrimidines with N-(1-chloroalkyl)amides of carboxylic acids and N-acylimines forms only the S-substituted products. How to Cite Klyuchko, S. V.; Khutova, B. M.; Prikazchikova, L. P. Chem. Heterocycl. Compd. 1994, 30, 1069. [Khim. Geterotsikl. Soedin. 1994, 1234.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171167
Functionally substituted azines. 1. Synthesis and reactions of 2-(N-cyano-N-carbethoxmethylamino)-4,6-dimethylpyrimidine
Treatment of 2-(N-potassium-N-cyanamino)-4,6-dimethylpyrimidine with ethyliodoacetate produces 2-(N-cyano-N-carbethoxymethylamino)-4,6-dimethylpyrimidine. Alkaline hydrolysis of the last gives 2-(3-potassium-2,4-dioxoimidazolidinyl-1)-4,6-dimethylpyrimidine. Ammonolysis and hydrazinolysis give imino- or amino-imidazolidinylpyrimidine, respectively. How to Cite Dovlatyan, V. V.; Éliazyan, K. A.; Pivazyan, V. A. Chem. Heterocycl. Compd. 1994, 30, 1074. [Khim. Geterotsikl. Soedin. 1994, 1239.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171168
Pyrrolopyrimidines. 1. Electrophilic substitution reactions of 1,3-dimethylpyrrolo[3,2-d]pyrimidine-2,4-dione
The reactions of halogenation, aminomethylation, acylation, and azo coupling in 1,3-dimethylpyrrolo[3,2-d]pyrimidine-2,4 dione proceed at position 7, whereas nitration in acetic acid is directed primarily to position 6. In a some of cases, products of substitution of both hydrogen atoms in the pyrrole ring have been synthesized. How to Cite Tsupak, E. B.; Tkachenko, Yu. N.; Pozharskii, A. F. Chem. Heterocycl. Compd. 1994, 30, 1077. [Khim. Geterotsikl. Soedin. 1994, 1242.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171169
Purines, pyrimidines, and condensed systems based on these compounds. 12. 1,3-Dimethylpyrimido[4,5-d]pyrimidine-2,4-(1H,3H)dione: The first case of regioselective amination of condensed pyrimidines in position 2
1,3-Dimethylpyrimido[4,5-d]pyrimidine-2,4-(1H,3H)dione (l) reacts with alkylamides in liquid ammonia in the presence of an oxidizing agent such as KMnO4 or Ag(C5H5N)2MnO4, giving 7-amino derivatives; but the interaction of (1) with methylamine gives a mixture of isomeric alkylaminated products. Subsequent hydrolysis of the 7-piperidino derivatives in an alkaline medium and then in an article medium gives 4-methylamino-2-piperidinopyrimidine with quantitative yield. How to Cite Gulevskaya, A. V.; Pozharskii, A. F.; Shorshnev, S. V.; Zheltushkina, E. A. Chem. Heterocycl. Compd. 1994, 30, 1083. [Khim. Geterotsikl. Soedin. 1994, 1249.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171170
Purines, pyrimidines, and condensed systems based on these compounds. 13. Transformation of fervenulin-1-oxide to 8-alkylaminotheophyllines under the action of alkylamines
Fervenulin-1-oxide undergoes reactions with secondary alkylamines in which the triazine ring is ruptured and 8-alkylaminotheophyllines are formed. The final product of the interaction of fervenulin-1-oxide with primary amines or with liquid ammonia is 1,3-dimethyl-5-imino-6-hydroximinouracil. How to Cite Gulevskaya, A. V.; Pozharskii, A. F.; Shvidchenko, S. V. Chem. Heterocycl. Compd. 1994, 30, 1087. [Khim. Geterotsikl. Soedin. 1994, 1253.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171171
Synthesis of 3-hydrazino-6-tert-butyl-1,2,4-triazolo[3,4-c]-1,2,4-triazin-5-one
3-Hydrazino-6-tert-butyl-1,2,4-triazolo[3,4-c]-1,2,4-triazin-5-one was synthesized by the reaction of a substituted 4-(N,N-dimethylcarbamoyl)-3-thioxo-1,2,4-triazine with hydrazine. The spectral characteristics and the proposed reaction mechanism are discussed. How to Cite Mironovich, L. M. Chem. Heterocycl. Compd. 1994, 30, 1092. [Khim. Geterotsikl. Soedin. 1994, 1258.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171172
Phosphorylnitrile oxides. 6. 1,3-cycloaddition with azomethines and nitriles
The 1,3-dipolar cycloaddition of diisopropoxyphosphorylnitrile oxide to Schiff bases gives 3-diisopropoxyphosphoryl-4-R-5-phenyl-1,2,4-oxadiazolines. The cycloaddition of phosphorylated nitrile oxides at the azomethine bond of hydrazones does not proceed due to the low dipolarophilic activity of the CH = N bond and high tendency of phosphorylnitrile oxidesto undergo dimerization and polymerization. The reaction of nitrile oxides with 2-hydroxybenzylidenaniline leads to the corresponding ester of diisopropoxyphosphorylformhydroxamic acid. The nitrile group undergoes cycloaddition only when activated. The reaction of a solution of phosphorylnitrile oxides in benzene with tetracyanoethylene gives the bisadduct at the two C = N bonds without affecting the C = C bond. How to Cite Pavlov, V. A.; Kurdyukov, A. I.; Moskva, V. V. Chem. Heterocycl. Compd. 1994, 30, 1095. [Khim. Geterotsikl. Soedin. 1994, 1261.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171173
Phosphorylinitrile oxides. 7. Quantum chemical study of the dimerization of nitrile oxides
A semiempirical MNDO calculation was carried out for the singlet potential energy surface for the dimerization of acetonitrile oxide leading to dimethylfuroxane. The dimerization of nitrile oxides proceeds by a two-step mechanism. The rate-limiting step is formation of a dinitrosoethylene intermediate. A semiempirical AMI calculation was carried out to study the effect of phosphoryl substituents on formation of the transition state of the rate-limiting step in the dimerization of dimethoxyphosphorylnitrile oxide. Independently of the initial orientation of the two phosphorylnitrile oxide molecules, a gauche-oriented dimeric species is formed in the first step in the dimerization. There is hardly any specific effect ofthe phosphoryl substituents in the first step of phosphorylnitrile oxide dimerization. How to Cite Kurdyukov, A. I.; Pavlov, V. A.; Gorin, B. I. Chem. Heterocycl. Compd. 1994, 30, 1101. [Khim. Geterotsikl. Soedin. 1994, 1269.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171174
Rearrangement of 2-iminoperhydrothieno-[3,4-d]thiazole 5,5-dioxides
The reaction of 4-bromo-2-thiolene 1,1-dioxide with thiosemicarbazide and thiosemicarbazones gave 2-iminoperhydrothieno[3,4-d]thiazole 5,5-dioxides, which contain a nitrogen function at the imino group. The recyclization of these compounds was studied. How to Cite Makarenko, A. G.; Parkhomenko, P. I.; Rozhenko, A. B.; Grigor'ev, A. A.; Rybakova, M. V.; Bezuglyi, Yu. V. Chem. Heterocycl. Compd. 1994, 30, 1106. [Khim. Geterotsikl. Soedin. 1994, 1274.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171175
Reactions of polyhalopyridines. 8. Reactions of polychlorotrifluoromethyl-pyridines with sodium N,N-dimethyldithiocarbamate. Structure of the 8-trifluoromethylbis-1,3-dithiolo-[4,5-b:4′,5′-e]-pyridine-2,6-dione molecule
The reaction of the isomeric tetrachloro-α-, β-, and γ-trifluoromethylpyridines and of 3,4,5-trichloro-2-trifluoromethylpyridine with sodium N,N-dimethyldithiocarbamate dihydrate has been studied. In the case of the α-, and γ-isomers an intramolecular cyclization with the formation of 1,3-dithiol-2-one derivatives occurs and the remaining compounds give only products of mono- or disubstitution of chlorine atoms by a dithiocarbamate fragment at positions 4 or 6 of the pyridine ring. The structure of the compounds synthesized was proved using 13C NMR and X-ray crystallographic analysis. How to Cite Sipyagin, A. M.; Aliev, Z. G. Chem. Heterocycl. Compd. 1994, 30, 1278. [Khim. Geterotsikl. Soedin. 1994, 1.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171176
Pyrimidotetrathiafulvalenes. 2. Trimethylsilylation of 5,-dioxo(4H,6H)-1,3-dithiolo[4,5-d]pyrimidine-2-selone and the use of the silylated product for the synthesis of 2,4-dioxopyrimidotetrathiafulvalenes
The trimethylsilylation of 5,7-dioxo(4H,6H)-1,3-dithiolo[4,5-d]pyrimidine-2-selone with bis(trimethylsilyl)acetamide enables pyrimido-tetrathiafulvalene derivatives to be prepared in benzene solution and increases the yield of the target compounds compared with the reaction of the unsilylated selone in DMF solution. The intermediate 2,4-bis(trimethylsilyloxy)pyrimidotetrathiafulvalenes were sensitive to hydrolysis. The previously undescribed [2,4-dioxo(1H,3H)pyrimido]di(methylthio)tetrathifulvalene has been obtained. The redox properties of the compounds obtained have been investigated by cyclic current-potential measurements. How to Cite Neiland, O. Ya.; Tilika, V. Z.; Edzhinya, A. S. Chem. Heterocycl. Compd. 1994, 30, 1116. [Khim. Geterotsikl. Soedin. 1994, 1285.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01171177