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Note | Regular issue | Vol 55, No. 11, 2001, pp.2189-2198
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9285
■ Reaction of N-Substituted 3,4-Dichloromaleimides with α-Mercaptoazaheterocycles

Galina G. Dubinina, Yulian M. Volovenko, Svetlana V. Shishkina, Oleg V. Shishkin, and Sergiy M. Yarmoluk*

*Institute of Molecular Biology and Genetics, National Academy of Sciences of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine

Abstract

Reaction of N-substituted 3,4-dichloromaleimides (1) with α-mer-captoazaheterocycles, 2-mercapto-1H-benzo[d]imidazole (2) and 3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazin-5-ones (4) in the presence of triethylamine, led to the formation of condensed thiazole ring resulting in 2,3-dihydro-1H-benzo[4,5]imidazo[2,1-b]pyrrolo[3,4-d][1,3]thiazole-1,3-diones (5) and 7,8-dihy-dro-2H,6H-pyrrolo[3’,4’:4,5][1,3]thiazolo[3,2-b][1,2,4]triazine-2,6,-8-triones (8), respectively. Refluxing of 8 in aqueous dioxane-triethylamine produced derivatives of 7-oxo-7H-[1,3]thiazolo[3,2-b][1,2,4]triazine-2-carboxamides (9) by destruction of maleimide ring with decarboxylation. The structure of 9i was confirmed by X-Ray analysis. 1 reacted with 2-thioxo-1,2,3,4-tetrahydro-4-quinazolinone (3) with cyclization at N-1 and N-3 positions.