N 71 Nitroalkyl-substituted tetrahydropyrazines in syntheses of azapolycyclic compounds [Electronic resource] / P. A. Slepukhin, N. N. Mochul`skaya, L. P. Sidorova, G. L. Rusinov, M. A. Ezhikova, M. I. Kodess, O. N. Kazheva, A. N. Chekhlov, O. A. Dyachenko, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2005. - Vol. 54, № 9. - P2197-2203. - Библиогр. : с. 2203 (13 назв. ) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Tri-and tetracyclic compounds were synthesized by the cyclization of 6-alkoxy-2,3-dicyano-5-nitromethyl-1,4,5,6-tetrahydropyrazines with 1,2,3-triazinium and quinoxalinium cations. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2005, 54 (9), 2197-2203.pdf |
S 59 Sigma(H)-Adducts of N-alkylpyrazinium and quinoxalinium salts with nucleophiles. The 1H and 13C NMR spectra and the crystal structures of P-adducts [Electronic resource] / E. V. Verbitskiy, M. V. Berezin, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 1. - P176-181 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The previously unknown addition products of P-nucleophiles to 5-aryl- and 5-hetaryl- 2,3-dicyano-1-ethylpyrazinium salts and to 5-aryl- and 5-hetaryl-14nethylquinoxalinium salts were synthesized. The three-dimensional structures of the P- sigma(H)-adducts of the 1,4-diazine series were established by X-ray diffraction \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (1), 176-181.pdf |
R 30 Reactions of N-alkylazinium cations. 2. Reaction of quinoxalinium salts with malonodinitrile and cyanoacetic ester [Electronic resource] / V. N. Charushin, O. N. Chupakhin, G. M. Petrova, E. O. Sidorov, N. A. Klyuev, L. G. Egorova // Chemistry of Heterocyclic Compounds. - 1981. - Vol. 17, № 2. - P189-194. - Bibliogr. : p. 194 (12 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): N-ALKYLQUINOXALINLUM SALTS -- MALONODINITRILE -- CYANOACETIC ESTER CARBANIONS Аннотация: N-Alkylquinoxalinlum salts react with malonodinitrile and cyanoacetic ester carbanions to give addition products, which, due to favorably disposed CN groups and active CH centers, subsequently undergo intramolecular cyclization with the formation of a five-membered ring. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1981, v.17, N 2, p.189.pdf |
C 98 Cyclization of n-alkylazinium cations with bisnucleophiles. 4. Regio- and stereospecificity of the reactions of β-diketones with quinoxalinium salts and their aza and benzo analogs [Electronic resource] / V. N. Charushin, M. G. Ponizovskii, O. N. Chupakhin, A. I. Rezvukhin, G. M. Petrova, Yu. A. Efremov // Chemistry of Heterocyclic Compounds. - 1981. - Vol. 17, № 11. - P1129-1134. - Bibliogr. : p. 1134 (10 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): QUINOXALINIUM -- PYRAZINIUM SALTS -- BISNUCLEOPHILES Аннотация: The reactions of substituted quinoxalinium, benzo[g]- and benzo[f]quinoxalinium, and pyrido[2,3-b]pyrazinium salts with anions of β-dicarbonyl compounds give furo[2,3-b]-annelated systems with strictly determined regio- and stereoorientations \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1981, v.17, N 11, p.1129.pdf |
C 98 Cyclization of N-alkylazinium cations with bisnucleophiles. 7. Reactions of quinoxalinium salts with α-substituted acetamides [Electronic resource] / V. N. Charushin, L. M. Naumova, G. G. Izmailova, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 1983. - Vol. 19, № 8. - P901-905. - Bibliogr. : p. 905 (5 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): QUINOX-ALINIUM SALTS -- ACETAMIDES Аннотация: Acetamides that contain acceptor substituents in the α position react with quinox-alinium salts to give cis-hexahydropyrrolo[2,3-b]quinoxalin-2-ones. Acetic acid arylamides are inert under these conditions. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1983, v.19, N 8, p. 901.pdf |
C 98 Cyclization of N-alkylazinium cations with binucleophiles. 8. Annellation of the imidazole ring with pyrazines and quinoxalines [Electronic resource] / V. N. Charushin, V. G. Baklykov, O. N. Chupakhin, N. N. Vereshchagina, L. M. Naumova, N. N. Sorokin // Chemistry of Heterocyclic Compounds. - 1983. - Vol. 19, № 12. - P1333-1338. - Bibliogr. : p. 1337-1338 (15 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINIUM ION -- QUINOXALINIUM ION Аннотация: Monosubstituted and N,N′-disubstituted thioureas enter into cyclization with pyrazinium and quinoxalinium ion to form imidazo[4,5-b]-annellated pyrazines and quinoxalines \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1983, v.19, N 12, p. 1333.pdf |
C 98 Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 11. Reactions of quinoxalinium salts with thioamides — Simple method for the synthesis of hydrogenated thiazolo[4,5-b]quinoxalines [Electronic resource] / V. G. Baklykov, V. N. Charushin, O. N. Chupakhin, V. N. Drozd // Chemistry of Heterocyclic Compounds. - 1984. - Vol. 20, № 5. - P554-558. - Bibliogr. : p. 558 (13 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): THIOACETAMIDES -- THIOBENZAMIDES -- N-ALKYLQUINOXALINLUM SALTS Аннотация: Thioacetamides and thiobenzamides undergo cyclization with N-alkylquinoxalinium salts in the presence of bases to give 4-alkyl-3a,4,9,9a-tetrahydrothiazolo[4,5-b]quinoxalines \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1984, v.20, N 5, p. 554.pdf |
C 98 Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 14. Reaction of quinoxalinium salts with mono- and N,N′-disubstituted amidines / L. M. Naumova, V. N. Charushin, O. N. Chupakhin, G. G. Izmailova // Chemistry of Heterocyclic Compounds. - 1985. - Vol. 21, № 3. - С. 326-331. - Bibliogr. : p. 330-331 (7 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BENZAMIDINES -- QUINOXALINUM SALTS Аннотация: Monosubstituted benzamidines undergo cyclization with quinoxalinum salts to give 1,2-disubstituted 3a,4,9,9a-tetrahydroimidazo[4,5-b]quinoxalines. The participation in similar cyclizations of N,N′-disubstituted amidines with a CH-active group in the a position leads to 3a,4,9,9a-tetrahydropyrrolo[2,3-b]quinoxalines \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1985, v.21, N 3, p. 326.pdf |
C 98 Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 15. Isomerization of thiazolo[4,5-b]quinoxalines in the presence of acids [Electronic resource] / V. N. Charushin, V. G. Baklykov, O. N. Chupakhin, V. N. Drozd // Chemistry of Heterocyclic Compounds. - 1985. - Vol. 21, № 3. - С. 331-338. - Bibliogr. : p. 337-338 (21 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ISOMERIZATION -- CHLOROFORM -- QUINOXALINIUM CATION Аннотация: 4-Alkyl-2-phenyl-3a,4,9,9a-tetrahydrothiazolo[4,5-b]quinoxalines undergo isomerization in chloroform in the presence of acids to the regioisomeric (with respect to them) 9-alkyl-substituted derivatives. Under the same conditions 2,4-dimethyl-3a,4-9,9a-tetrahydrothiazolo [4,5-b]quinoxaline undergoes isomerization to 4-methyl-1H-2,3,3a,4,9,9a-hexahydropyrrolo[2,3-b]quinoxaline-2-thione. It was demonstrated by means of deuterium labels that in both cases the isomerization proceeds through a step involving dissociation to a quinoxalinium cation and the corresponding thioamide \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1985, v.21, N 3, p. 331.pdf |
C 98 Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 16. σ-adducts of quinoxalinium salts with amines, alcohols, and enolates and their role in cyclizations with β-dicarbonyl compounds [Electronic resource] / V. N. Charushin, M. G. Ponizovskii, O. N. Chupakhin, E. O. Sidorov, I. M. Sosonkin // Chemistry of Heterocyclic Compounds. - 1985. - Vol. 21, № 5. - С. 564-572. - Bibliogr. : p. 571-572 (16 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ACETYLACETONE -- 1H NMR SPECTROSCOPY -- N-METHYLQUINOXALINIUM CATION Аннотация: In the reaction of N-methylquinoxalinium iodide with acetylacetone at −30 °C, the formation of 3-acetyl-2,4-dimethyl-3a,4,9,9a-tetrahydrofuro[2,3-b]quinoxaline has been recorded by 1H NMR spectroscopy, this being a regioisomer of the 3-acetyl-2,9-dimethyl-3a,4,9,9a-tetrahydro[2,3-b]quinoxaline formed in this reaction at temperatures above −10 °C. σ-Adducts of the N-methylquinoxalinium cation with alcohols, amines, and β-diketones have also been identified, and their role in cyclizations leading to the annelation of a furan ring is discussed. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1985, v.21, N 5, p. 564.pdf |
C 98 Cyclization of N-alkylammonium cations with bifunctional nucleophiles. 17. Annelation of imidazole and 1,2,4-triazine rings with pyrazines via the reactions of thiosemicarbazides with pyrazinium salts [Electronic resource] / V. G. Baklykov, V. N. Charushin, O. N. Chupakhin, N. N. Sorokin // Chemistry of Heterocyclic Compounds. - 1985. - Vol. 21, № 7. - С. 798-804. - Bibliogr. : p. Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,4-DISUBSTITUTED THIOSEMICARBAZIES -- CYCLIZATION REACTIONS -- THIOSEMICARBAZIDES Аннотация: 1- and 4-mono- as well as 1,4-disubstituted thiosemicarbazies undergo cyclization reactions upon treatment with N-alkylpyrazinium and quinoxalinium salts to give N-aminosubstituted imidazo[4,5-b]pyrazines and imidazo[4,5-b]quinoxalines, respectively. Thiosemicarbazides containing substituents in the 2-position react with N-alkylquinoxaline salts to give 1,2,4-triazino[5,6-b]quinoxalines after cyclization. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1985, v.21, N 7, p. 798.pdf |
R 30 Reactions of azinium ions. 4. Reactions of quinoxalinium salts with nitroalkanes — Single-stage path to tetraazaheterocycles with bridged and framework structures [Electronic resource] / V. N. Charushin, G. M. Petrova, O. N. Chupakhin, E. O. Sidorov, G. G. Aleksandrov, A. I. Chernyshev, N. A. Klyuev, N. N. Sorokin // Chemistry of Heterocyclic Compounds. - 1986. - Vol. 22, № 3. - С. 318-328. - Bibliogr. : p. 327-328 (11 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINIUM IONS -- QUINOXALINUM SALTS -- NITROALKANES Аннотация: The addition of the carbanions of nitroalkanes of N-alkylquinoxalinium salts in an alcohol medium leads to dibenzo [d,k]-1,3,6,10-tetrasubstituted tricyclo[7.3.1.02,7]-and tetracyclo[7.3.1.02,706,13]tridecanes. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1986, v.22, N 3, p. 318.pdf |
C 98 Cyclization of N-alkyl azinium cations with bifunctional nucleophiles. 21. Regioisomeric 1,3,4-thiadiazino[5,6-b]quinoxalines [Electronic resource] / V. G. Baklykov, V. N. Charushin, O. N. Chupakhin, V. N. Drozd // Chemistry of Heterocyclic Compounds. - 1987. - Vol. 23, № 4. - С. 465-469. - Bibliogr. : p. 469 (9 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): THIOBENZHYDRAZIDES -- N-ALKYL-QUINOXALINIUM SALTS -- THIADIAZINOQUINOXALINES Аннотация: Thiobenzhydrazides undergo cyclization with N-alkyl-quinoxalinium salts to give 5-alkyl-substituted 1,4,4a,5,10,10a-hexahydro-1,3,4-thiadiazino[5,6-b]quinoxalines, which undergo isomerization to 10-alkyl-substituted thiadiazinoquinoxalines when they are heated in ethanol or in the presence of acids \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1987, v.23, N 4, p. 465.pdf |
N 30 Naumova, L. M. Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 24. Synthesis of condensed 1,2,4-triazino- and 1,2,4-oxadiazino[5,6-b]quinoxaline systems [Electronic resource] / L. M. Naumova, V. N. Charushin, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 1987. - Vol. 23, № 8. - С. 895-899. - Bibliogr. : p. 898-899 (19 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CYCLIZATION -- QUINOXALINUM SALTS -- AMIDHYDRAZONES Аннотация: Cyclization of quinoxalinium salts with amidoximes and amidhydrazones yields partially hydrogenated derivatives of new 1,2,4-oxadiazino- and 1,2,4-triazino[5,6-b]quinoxaline heterocyclic systems. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1987, v.23, N 8, p. 895.pdf |
C 98 Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 23. Electrochemical criteria for electrophilicity in 1,4-diazinium cations and their participation in cyclizations with acetoacetamide [Electronic resource] / I. M. Sosonkin, G. L. Kalb, I. V. Kazantseva, M. G. Ponizovskii, V. N. Charushin, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 1987. - Vol. 23, № 8. - С. 888-895. - Bibliogr. : p. 894-895 (22 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINIUM -- QUINOXALINIUM -- BENZOQUINOXALINIUM Аннотация: The polarographic reduction potentials E1/2 of the pyrazinium, quinoxalinium, benzoquinoxalinium, pyrido[2,3-b]pyrazinium, and pteridinium cations were determined. Annellation of a benzene ring increases the electrophilicity of the diazinium cations to a greater degree than the introduction of such electron acceptors as aza, aminocarbonyl, or methoxycarbonyl groups. The boundary between the active and inactive 1,4-diazinium salts was determined; cations with E1/2 values more negative than −0.50 V do not form either stable covalent adducts or cyclic diadducts through annellation of the dinucleophiles to the pyrazine ring. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1987, v.23, N 8, p. 888.pdf |
R 30 Reactions of azinium cations. 7. 13C NMR spectra and electron structure of neutral σ-adducts of 1,4-diazinium cations and methylate anion [Electronic resource] / O. N. Chupakhin, V. N. Charushin, I. V. Kazantseva, M. G. Ponizovskii, E. O. Sidorov, P. A. Torgashev, A. V. Belik // Chemistry of Heterocyclic Compounds. - 1987. - Vol. 23, № 10. - С. 1112-1117. - Bibliogr. : p. 1116-1117 (23 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NMR SPECTRA -- σ-ADDUCTS -- PYRAZINIUM Аннотация: The 13C NMR spectra have been recorded of a number of σ-adducts formed by pyrazinium, quinoxalinium, and pteridinium cations with methylate anion. The experimental data were compared with CNDO/2 calculations of adduct electron structure. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1987, v.23, N 10, p. 1112.pdf |
C 98 Cyclizations of N-alkyl-substituted azinium cations with bifunctional nucleophiles. 28. Orientation of the nucleophile in the reaction of quinoxalinium salts with indan-1,3-dione [Electronic resource] / G. M. Petrova, M. G. Ponizovskii, V. N. Charushin, G. G. Aleksandrov, E. O. Sidorov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 1990. - Vol. 26, № 5. - С. 565-572. - Bibliogr. : p. 572 (12 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): QUINOXALINUM SALTS -- C-NUCLEOPHILES -- AZINIUM CATIONS Аннотация: In reactions with quinoxalinium salts in alcoholic-base media indan-1,3-dione acts as a C nucleophile, adding at the 2 or 3 position of the heterocycle to give the corresponding ylidene derivatives; attack by the nucleophile at the C(3) atom (the Β position relative to the quaternary nitrogen atom) is preceded by addition of alcohol at the a position. Dissociative substitution at the C(2) atom in 2-alkoxy-3-(1,3-dioxoindan-2-ylidene)-1,2,3,4-tetrahydroquinoxalines by another nucleophile makes it possible to regard lyate complexes as probable intermediates in cyclizations of 1,4-diazinium salts with dinucleophiles. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1990, v.26, N 5, p.565.pdf |