Synthesis and Transformations of 9-Substituted Imidazo[1,2-a]benzimidazole-2-carbaldehydes

doi:10.1134/S1070428020070064

Paper

Synthesis and Transformations of 9-Substituted Imidazo[1,2-a]benzimidazole-2-carbaldehydes

Published Jul 1, 2020 · T. A. Kuzʼmenko, L. Divaeva, A. Morkovnik

Russian Journal of Organic Chemistry

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Abstract

Ethyl 2-formyl-9-methyl-9H-imidazo[1,2-a]benzimidazole-3-carboxylate was synthesized for the first time in a high yield by heating a solution of ethyl 2-(dibromomethyl)-9-methyl-9H-imidazo[1,2-a]benzimidazole-3-carboxylate in ethanol. Acid hydrolysis of the product gave less accessible 9-methylimidazobenzimidazole-2-carbaldehyde. Ethyl 2-formyl-9-methyl-9H-imidazo[1,2-a]benzimidazole-3-carboxylate underwent cyclization to fused oxopyridazine derivative by treatment with hydrazine hydrate, it reacted as a typical aldehyde with acetophenones, hydroxylamine hydrochloride, and malononitrile, and its reaction with acetylacetone and thiourea (Biginelli reaction) afforded the corresponding pyrimidine derivative.

Study Snapshot

This study successfully synthesized and transformed ethyl 2-formyl-9-methyl-9H-imidazo[1,2-a]benzimidazole-3-carboxylate, a key intermediate in the Biginelli reaction, in a high yield.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis and Transformations of 9-Substituted Imidazo[1,2-a]benzimidazole-2-carbaldehydes

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