S 69 S-N(H)-Reactions of triazolo[4,3-b]- and tetrazolo[1,5-b]-1,2,4-triazines with methylene-active carbonyl compounds [Electronic resource] / G. L. Rusinov, N. A. Itsikson, D. G. Beresnev, M. I. Kodess, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2001. - Vol. 50, № 11. - P2183-2187 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Unsubstituted triazolo[4,3-b]- and tetrazolo[1,5-b]-1,2,4-triazines react with carbanions generated from dimedone and barbituric acid to give adducts of a C-nucleophile with the heterocyclic system through the C=N double bond. The adducts can be oxidized under mild conditions into products of nucleophilic hydrogen substitution. Analogous adducts with carbanions produced in the reactions of ethyl cyanoacetate and ethyl malonate with ButOK proved to be unstable; in this case, the title azolotriazines immediately yield products of nucleophilic hydrogen substitution in position 7. Tautomerism of the S N H products obtained is discussed. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2001, 50 (11), 2183.pdf |
R 30 Reactions of 3-phenyl-1,2,4-triazine with some C-nucleophiles [Electronic resource] / Y. A. Azev, O. S. Ermakova, M. I. Kodess, M. A. Ezhikova, I. S. Kovalev, V. A. Bakulev // Mendeleev Communications. - 2013. - Vol.23. - С. 294-296. - Bibliogr. : p. 296 (5 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): C-NUCLEOPHILES -- 1,2,4-TRIAZINE -- AMIDRAZONE Аннотация: Dimedone is added at C(5) of 3-phenyl-1,2,4-triazine to give stable dihydro derivative. Its reaction with 1-aryl-3-methylpyrazol-5- ones proceeds with fragmentation affording 1,1,2,2-tetrakispyrazolylethane and amidrazone derivatives \\\\expert2\\nbo\\Mendeleev Communications\\2013, v.23, p. 294-296.pdf |
N 52 New opportunities for the synthesis of quinoxaline-substituted heterocyclic and aryl moieties [Electronic resource] / Y. A. Azev, M. I. Kodess, M. A. Ezhikova, A. M. Gibor, V. I. Baranov, O. S. Ermakova, V. A. Bakulev // Pharmaceutical Chemistry Journal. - 2013. - Vol.47, №9. - С. 498-502. - Bibliogr. : p. 502 (10 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DIMEDONE -- INDANDIONE -- DMSO SOLUTION Аннотация: 6.7-Difluoroquinoxaline (I) reacted with dimedone, indandione, and 3-methyl-1-phenylpyrazol-5-one in DMSO solution in the presence of acid to form mono-substituted products IIa - c. Heating I with resorcinol in EtOH in the presence of acid gave resorcinol derivative IId. 6.7-Difluoroquinoxaline in the presence of base reacted with 3-methyl-1-phenylmethylpyrazol-5-one to form dipyrazolylmethane III and tetrapyrazolylethane derivative IV. Heating products IIa - c with N-methylpiperazine produced 7-methylpiperazine derivatives Va - c of 2-substituted quinoxalines \\\\expert2\\nbo\\Pharmaceutical Chemistry Journal\\2013, 47 (9), 498.pdf |