Cyclization of n-alkylazinium cations with bisnucleophiles. 5. Cyclic adducts and recyclization products in the reactions of benzodiazinium cations with imido esters

Cyclization of n-alkylazinium cations with bisnucleophiles. 5. Cyclic adducts and recyclization products in the reactions of benzodiazinium cations with imido esters / O. N. Chupakhin, V. N. Charushin, L. M. Naumova, A. I. Rezvukhin, N. A. Klyuev // Chemistry of Heterocyclic Compounds. - 1981. - Vol. 17, № 11. - P. 1134-1138. - Bibliogr. : p. 1138 (23 ref.).

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1981

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статья из журнала

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Аннотация

The reaction of imido esters that contain an active methylene group with four isomeric benzodiazinium cations, viz., the 1-methylquinoxalinium, 2-methylcinnolinium, 3-methylquinazolinium, and 2-methylphthalazinium cations, was investigated. The 1-methylquinoxalinium cation reacts with imido esters via a scheme involving anionic [3- +2]-cycloaddition to form tetrahydropyrrolo[2,3-b]quinoxalines. The 2-methylcinnolinium cation forms an adduct with an annelated pyrrole ring. Under the influence of imido esters, the 3-methylquinazolinium cation undergoes recyclization to a 2,3-disubstituted quinoline. The 2-methylphthalazinium cation is inert in this reaction.