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
Dihydroazolopyrimidines with a nodal nitrogen atom: Synthesis, reactions, tatutomerism
The published data on methods of synthesis of dihydro derivatives of azolopyrimidines with a nodal nitrogen atom are generalized; their applicability is comparatively analyzed. The chemical properties of dihydroazolopyrimidine systems are examined; the intra- and intermolecular factors that determine the position of imine—enamine tautomeric equilibrium are analyzed. How to Cite Desenko, S. M. Chem. Heterocycl. Compd. 1995, 31, 125. [Khim. Geterotsikl. Soedin. 1995, 147.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169665
Copyright (c) 2026 Chemistry of Heterocyclic Compounds
ОБЗОРЫ ПО ОТДЕЛЬНЫМ ВОПРОСАМ ХИМИИ ГЕТЕРОЦИКЛОВ
Как ссылаться Химия гетероцикл. соединений 1995, 276.
ОБЗОРЫ, КАСАЮЩИЕСЯ БИОЛОГИЧЕСКИ АКТИВНЫХ ГЕТЕРОЦИКЛОВ
Как ссылаться Химия гетероцикл. соединений 1995, 278.
ОБЗОРЫ ПО ОБЩИМ ВОПРОСАМ ОРГАНИЧЕСКОЙ ХИМИИ, ЗАТРАГИВАЮЩИЕ ХИМИЮ ГЕТЕРОЦИКЛОВ
Как ссылаться Химия гетероцикл. соединений 1995, 281.
Reaction of substituted 1,3-dioxanes with the disobutyl ester of isobutylboric acid
The reaction of subsitituted 1,3-dioxanes with the diisobutyl ester of isobutylboric acid leads to the corresponding 1,3,2-dixaborinanes. The determining factor in the reactivity of the 1,3-dioxanes is the degree of substitution of the acetal atom. How to Cite Kuznetsov, V. V.; Tereshchenko, A. V.; Gren', A. I. Chem. Heterocycl. Compd. 1995, 31, 137. [Khim. Geterotsikl. Soedin. 1995, 160.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169666
Alkylation of N-methylpyrrole with tert-butanol in the presence of Amberlyst 15 ion exchanger
The 2- and 3-tert-butylderivatives of 1-methylpyrrole, hitherto unknown, have been obtained by a single-stage method. The process is characterized by a low positional selectivity with a somewhat predonminating β-substitution. The results have been compared with data, obtained by the quantum-chemical calculation of the molecules of pyrrole, N-methylpyrrole, and also of their σ-complexes with protons, introduced in the α- and β-position of the rings. How to Cite Iovel', I.; Fleisher, M.; Popelis, Yu.; Shimanska, M.; Lukevits, E. Chem. Heterocycl. Compd. 1995, 31, 140. [Khim. Geterotsikl. Soedin. 1995, 163.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169667
Heterocyclization of N-propionylaminoindoline
Treatment of N-propionylaminoindoline with a solution of phosgene in benzene gives the 1-[(indolin-1-yl)imino]propyl ester of 7-(1-cyanoethyl)indoline-1-carboxylic acid. The structure of the compound was proved using 1H and 13C NMR spectroscopy. How to Cite Zhestkov, V. P.; Barinova, V. N.; Portnov, Yu. N.; Chernyshev, A. I. Chem. Heterocycl. Compd. 1995, 31, 144. [Khim. Geterotsikl. Soedin. 1995, 168.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169668
Aggregation properties of copper dibenzobarrelenophthalocyanine
Depending on the solvent in which they are placed or from which they have been obtained, sterically hindered copper octa-tert-butyltetra-4,5-dibenzobarrelenophthalocyanines in solution and as a powder can take a monomeric form or dimer or trimer aggregate forms. In the aggregates, the molecules are disposed opposite one another around a high-order axis at an angle of 45° from equatorial displacement. How to Cite Selyutin, G. E.; Podrugina, T. A.; Gal'pern, M. G.; Luk'yanets, E. A. Chem. Heterocycl. Compd. 1995, 31, 146. [Khim. Geterotsikl. Soedin. 1995, 171.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169669
Synthesis of pyrazoles from ethyl-3-diazopyruvate
1,3-Dipolar cycloaddition to ethyl-3-diazopyruvate and its hydrazide gives the corresponding polycarbonyl pyrazoles. How to Cite Sukhotin, A. V.; Kartsev, V. G.; Kobrakov, K. I.; Serov, A. B. Chem. Heterocycl. Compd. 1995, 31, 150. [Khim. Geterotsikl. Soedin. 1995, 176.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169670
Photoinduced N-β-hydroxyalkylation of tropan derivatives
The photooxidation of tropan derivatives by ketones was studied; the targeting of the reaction to the N-CH3 group with the formation of N-alkylation products and bis-tropan derivatives was demonstrated. The presence of two diastereomers in salts of N-alkyl derivatives of tropan was detected by PMR spectroscopy. An alternative method of synthesis of difficult-to-obtain amino alcohols was proposed. How to Cite Kostochka, L. M.; Skoldinov, A. P.; Lezina, V. P. Chem. Heterocycl. Compd. 1995, 31, 153. [Khim. Geterotsikl. Soedin. 1995, 179.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169671
The molecular complex of 4-(N-pyridinium)pyridine-N-oxide chloride with tetracyanoethylene in the synthesis of substituted pyridine N-oxides
The structure of the complex of 4-(N-pyridinium)pyridine-N-oxide chloride with tetracyanoethylene was studied by 13C NMR spectroscopy. The results of the investigation, suggesting the use of this complex in the synthesis of substituted pyridine derivatives, were conformed experimentally by its reaction with oxygen- and nitrogen-containing nucleophiles. How to Cite Rodina, L. L.; Ryzhakov, A. V.; Alekseeva, O. O. Chem. Heterocycl. Compd. 1995, 31, 157. [Khim. Geterotsikl. Soedin. 1995, 184.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169672
Synthesis and properties of dithioacetals of conformationally constrained α-acyl-β-aminovinyl ketones of the 8-azasteroid
We have studied the reaction of α-acyl-β-aminovinyl of the 8-azasteroid series with ethanedithiol. The occurrence and orientation of the reaction are determined by structural and steric factors. As applied to derivatives of 8-azasteroids of the D-homo series, the reaction is irreversible and consequently the dithioacetal derivatives of this series are easily hydrolysed under acid and base conditions. Desulfurization over Raney nickel of the 17-dithioacetal derivative of 8-azagona-12,17-dione occurs with simultaneous dehydrogenation of the C ring and leads to the 17-deoxo-9,11-dehydro, while desulfurization of the 1-dithioacetal of 8-aza-D-homogona-12,17a-dione leads to the 12-deoxo derivative. By reaction of the 12-dithioacetal of 8-aza-D-homogona-17a-one with hydroxylamine, we obtained the 12-oximino derivative, which is the result of an unusual reaction at the site of the spiro coupling of the dithiolane ring with the 8-azasteroid ring. How to Cite Gulyakevich, O. V.; Mikhal'chuk, A. L.; Akhrem, A. A. Chem. Heterocycl. Compd. 1995, 31, 160. [Khim. Geterotsikl. Soedin. 1995, 187.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169673
4-Hydroxy-2-quinolones. 20. Synthesis and chemical conversions of ehtyl esters of the chloro-substituted quinoline-3-carboxylic acids
Preparative methods for the synthesis of ethyl esters of 2,4-dichloro- and 2-oxo-4-chloroquinoline-3-carboxylic acids were developed. The behavior of the compounds indicated was studied under conditions of alkaline and acidic hydrolysis, in reactions with some nucleophilic reagents, as well as in reductive dehalogenation. Results of the study of the antimicrobial and anti-inflammatory activity of the synthesized compounds are presented. How to Cite Ukrainets, I. V.; Taran, S. G.; Gorokhova, O. V.; Marusenko, N. A.; Kovalenko, S. N.; Turov, A. V.; Filimonova, N. I.; Ivkov, S. M. Chem. Heterocycl. Compd. 1995, 31, 167. [Khim. Geterotsikl. Soedin. 1995, 195.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169674
4-Hydroxy-2-quinolones. 26. Bromination of 3-substituted 2-oxo-4-hydroxyquinolones
The bromination of 3-alkyl- and 3-ethoxycarbonyl-2-oxo-4-hydroxyquinolones by molecular bromine gave 3-bromo-3-R-2,4-dioxoquinolones. Under analogues conditions, 1-R-2,4-dioxo-3H-quinolone-3-carboxylic acids form 1-R-3-bromo-2-oxo-4-hydroxyquinolones. The results of the study of the antimicrobial activity of the compounds synthesized are presented. How to Cite Ukrainets, I. V.; Taran, S. G.; Evtifeva, O. A.; Gorokhova, O. V.; Filimonova, N. I.; Turov, A. V Chem. Heterocycl. Compd. 1995, 31, 176. [Khim. Geterotsikl. Soedin. 1995, 204.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169675
Investigation of bisheteryl derivatives of piperazine and its analogs. 2. Synthesis and properties of bis(dialkyldithiocarbamoyl-5-nitro-4-pyrimidyl)piperazines
The corresponding 6-dialkyldithiocarbamoyl derivatives are obtained by reacting N,N′bis(2-R-6-chloro-5-nitro-4-pyrimidyl)carbamates. in one example it was shown that these products may be rearranged on heating with the formation of the bis(1,3-dithiolo[4,5-d]pyrimidyl)piperazine system, and in the presence of an alkaline catalyst may be converted by fission of the pyrimidine ring into the highly polarized N,N′-bis(1-amino-2-cyano-2-nitro-1-ethenyl)piperidine. How to Cite Makarov, V. A.; Sedov, A. L.; Nemeryuk, M. P.; Solov'eva, N. P.; Anisimova, O. S.; Safonova, T. S. Chem. Heterocycl. Compd. 1995, 31, 180. [Khim. Geterotsikl. Soedin. 1995, 208.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169676
Iodocyclization of 2-allythio-4(3H)-pyrimidinones
It has been established that the iodocyclization of 2-allythio-4-(3H)-pyrimidinones occurs at the N(1) nitrogen atom with the formation of 3-iodomethyl-7-oxo-2,3-dihydro-8H-thiazolo[3,2-a]pyrimidinium iodides and triiodides. How to Cite KKhim, D.G., Shmygarev, V.I. Chem. Heterocycl. Compd. 1995, 31, 183. [Khim. Geterotsikl. Soedin. 1995, 211.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169677
Synthesis and properties of derivatives of sym-triazine. 15. Synthesis of amine derivatives of sym-triazine that contain indole groups
By the cyclocondensation of imino esters of acids of the indole series with N-acylguanidines, 2-amino-4,6-disubstituted sym-triazines are obtained that contain indole groups. The reaction of N-(indolyl-3-imidolyl)guanidine with esters of carboxylic acids leads to 2-amino-4-(3-indolyl)-6-substituted sym-triazines. Indolyl-containing N-subsitituted 2,4-diamino-sym-triazines are synthesized by the reaction of imino esters of indole acids with biguanides. Similar products are also formed when 2-amino-4-trichloromethyl-sym-triazines that contain indole substituents react with dimethylamine, morpholine, or furfurylamine. How to Cite Kelarev, V. I.; Koshelev, V. N.; Morozova, G. V.; Karakhanov, R. A.; Remizov, A. S. Chem. Heterocycl. Compd. 1995, 31, 186. [Khim. Geterotsikl. Soedin. 1995, 214.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169678
Synthesis and properties of derivatives of sym-triazine. 16. Synthesis of amine and diamine derivatives of sym-triazine containing sterically hindered phenol groups from 6-alkyl(aryl)thio-2,4-bis(trichloromethyl)-sym-triazine
The reaction of 6-alkyl(aryl)thio-2,4-bis(trichloromethyl)-sym-triazines with ammonia and primary and secondary amines is studied. It is shown that, depending on the reaction conditions, the replacement of either one or both of the trichloromethyl groups takes place. 6-Alkyl(aryl)thio-2,4-diamino-sym-triazines containing sterically hindered phenol groups are synthesized. How to Cite Kelarev, V. I.; Koshelev, V. N.; Belov, N. V.; Malova, O. V.; Karakhanov, R. A. Chem. Heterocycl. Compd. 1995, 31, 195. [Khim. Geterotsikl. Soedin. 1995, 224.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169679
Synthesis of several heteryldehydropeptides by the oxazolone method
(E)-N-Benzolydehydro-3-(3-pyridyl)-alanyltryptophan was synthesized in 89% yield by the reaction of 2-phenyl-4-(3-pyridylidene)-5(4H)-oxazolone with tryptophan. The reaction of 4-[1-(2-furyliden)ethyl]- and 4-(3-pyridyliden)-2-phenyl-5(4H)-oxazolones with alanyltryptophan gives a mixture of the Z and E isomers of the corresponding dehydrotripeptides. Racemization of the alanyl and tryptophan residues was not observed. How to Cite Slavinskaya, V. A.; Sile, D. É.; Katkevich, M.; Korchagova, É. Kh.; Lipsbergs I. U.; Turovskii, I. V.; Lukevits, É. Chem. Heterocycl. Compd. 1995, 31, 202. [Khim. Geterotsikl. Soedin. 1995, 232.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169680
New 4(5H)-oxazolonium perchlorate derivatives
The condensation of 2,3-dimethyl-4(5H)-oxazolonium salts with ethyl orthoformate and amides of 5-substituted 2-furancarboxylic acids gives the corresponding products derived by modification of the methyl group at C(2), 2-formylmethylene-4-oxazolidinone and 2-furoylaminoethenyl-4(5H)-oxazolanium perchlorates. How to Cite Kosulina, T. P.; Kozlovskaya, I. N.; Bychenko, N. V.; Morenets, I. P.; Kul'nevich, V. G. Chem. Heterocycl. Compd. 1995, 31, 206. [Khim. Geterotsikl. Soedin. 1995, 236.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169681
Synthesis and properties of furan derivatives. 4. Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles containing furan fragments
The condensation of hydrochloride sats of iminoesters of furan acids with hydrazides of carboxylic acids gives 2,5-disubstituted 1,3,4-oxadiazoles containing furan fragments. Such compounds are also formed in the condensation of hydrazides of 5-R-furan-2-carboxylic acids with hydrocloride salts of carboxylic acid iminoesters. The reaction of furan acids with hydrazine dihydrochloride in polyphosphoric acid gave symmetrically disubstituted 1,3,4-oxadiazoles containing furan fragments. How to Cite Karakhanov, R. A.; Kelarev, V. I.; Koshelev, V. N.; Morozova, G. V.; Dibi, A. Chem. Heterocycl. Compd. 1995, 31, 208. [Khim. Geterotsikl. Soedin. 1995, 238.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169682
Synthesis of dihydro-10H-pyrano[3′,4′: 5,6]pyrido[3,2:4″,5″]-thieno[3″,2″-d][3,1]oxazines and -pyrimidines
Convenient methods have been developed for synthesizing dihydro-10H-pyrano[3′,4′:5,6]pyrido[3,2:4″,5″]thieno[3″,2″-d][3,1]-oxazines and -pyrimidines. Optimum conditions have been established for the chlorodeoxygenation of condensed thienopyrimidin-4-ones. How to Cite Dabaeva, V. V.; Noravyan, A. S.; Enokyan, B. D. Chem. Heterocycl. Compd. 1995, 31, 219. [Khim. Geterotsikl. Soedin. 1995, 250.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169683
Synthesis and stereochemistry of chiral azetidin-2-ones and azetidine-2-thiones. 3. Stereodirected construction of the β-lactam fragment of the thienamycin molecule
It has been shown possible to introduce an α-hydroxyethyl group trans-stereospecifically into position 3′ of 4-methyl-1-(α-methyl-benzyl)azetidin-2-one. The stereochemistry of the asymmetric centers C(3′), C(3), and C(4) of the diastereoisomers of the 3-α-hydroxyethyl derivative obtained in larger amount and of the corresponding three adjacent chiral centers C(8), C(6), and C(5) in thienamycin are the same. How to Cite Romanova, N. N.; Tallo, T. G.; Bundel, Yu. G. Chem. Heterocycl. Compd. 1995, 31, 223. [Khim. Geterotsikl. Soedin. 1995, 254.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169684
ESR spectra of electrochemically generated free anion radicals of hetaryl-substituted trichloro-1,4-benzoquinones
The ESR method was used to confirm the formation of free anion radicals in the source of electrochemical reduction of 5-thiazolyl-substituted 1,4-benzoquinones and related compounds, as well as the ability of the unpaired electron to become delocalized over the system of π electrons not only of the benzoquinone nucleus but also of the hetaryl substituent added to it. How to Cite Stradyn', Ya.; Gavars, R.; Baumane, L.; Valters, R. Chem. Heterocycl. Compd. 1995, 31, 227. [Khim. Geterotsikl. Soedin. 1995, 258.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169685
Gain in magnetic shielding of the 15N nucleus in a successive series of related 10, 12, and 14 π-electron heterocycles: 2,1,3-bensothiadiazole, 1,3,2,4-benzodithiadiazine, and 1,3,5,2,4-benzotrithiadiazine
A significant (≈85 ppm) increase in shielding of the 15N nucleus is observed in the successive series of 10, 12, and 14 π-electron heterocycles: 2,1,3-benzothiadiazole, 1,3,2,4-benzodithiadiazine, and 1,3,5,2,4-benzotrithiadiazine, as compared to the gain from both the full and the π-charge of the nitrogen atom. Possible antiaromaticity of the 12 π-electron dithiadiazine, containing a low-lying activation state, does not appear clearly in the 15N NMR. How to Cite Shakirov, M. M.; Beregovaya, I. V.; Zibarev, A. V. Chem. Heterocycl. Compd. 1995, 31, 231. [Khim. Geterotsikl. Soedin. 1995, 262.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169686
Synthesis of 11-N-arylaminomethylene derivatives of 8-azasteroies. A new rection of cyclic Schiff's bases
How to Cite Gulyakevich, O. V.; Mikhail'chuk, A. L.; Akhrem, A. A. Chem. Heterocycl. Compd. 1995, 31, 235. [Khim. Geterotsikl. Soedin. 1995, 266.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169687
Cyclization of 5-diazoimidazole-4-carbonitrile
How to Cite Mokrushin, V. S.; Pospelova, T. A.; Shafran, Yu. M. Chem. Heterocycl. Compd. 1995, 31, 237. [Khim. Geterotsikl. Soedin. 1995, 267.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169688
How to Cite Shelyakin, V. V.; Dyachenko, V. D.; Sharanin, Yu. A. Chem. Heterocycl. Compd. 1995, 31, 239. [Khim. Geterotsikl. Soedin. 1995, 269.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169689
Reaction of amino-imino-1H-isoindole with α-bromoketones
Как ссылаться Gordienko, O. V.; Lyubchuk, T. V.; Balitskii, Yu. V.; Kornilov, M. Yu. Chem. Heterocycl. Compd. 1995, 31, 241. [Химия гетероцикл. соединений 1995, 270.] Статья в английском издании журнала: DOI https://doi.org/10.1007/BF01169690
Synthesis of 2-oxooxazolo[5,4-b]pyridines and their reactions with amines
How to Cite Gudrinietse, É.; Yure, M.; Pastors, P.; Karklinya, A.; Palitis, É. Chem. Heterocycl. Compd. 1995, 31, 243. [Khim. Geterotsikl. Soedin. 1995, 271.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169691
1-Methyl-2-alkylbenzimidazole organomagnesium compounds
How to Cite Koshchienko, Yu. V.; Ryabtsova, O. V.; Tertov, B. A. Chem. Heterocycl. Compd. 1995, 31, 245. [Khim. Geterotsikl. Soedin. 1995, 272.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169692
Synthesis of N-ethoxycarbonyl-β-aminoketones —key intermediated for the preparation of nitrogen-containing heterocycles
How to Cite Sivova, N. V.; Shutalev, A. D. Chem. Heterocycl. Compd. 1995, 31, 246. [Khim. Geterotsikl. Soedin. 1995, 273.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169693
Reaction of cyclic sulfites with acetonitrile
How to Cite Kuznetsov, V. V. Chem. Heterocycl. Compd. 1995, 31, 248. [Khim. Geterotsikl. Soedin. 1995, 275.] For this article in the English edition, see DOI https://doi.org/10.1007/BF01169694