Abstract

1-Substituted benzimidazoles react with acylacetylenes and water (reflux in MeCN, 46–120 h) to stereoselectively give functionalized arylaminovinyl ketones, products of the imidazole ring-opening, in up to 75% yield and benzodiazocinones, products of the imidazole ring-expansion, in up to 28% yield. With D2O the yield of benzodiazocinone from 1-methylbenzimidazole and benzoylphenylacetylene is twice as much compared to the same reaction with H2O, thus demonstrating the strong isotopic effect of deuterium. The reaction mechanism, which agrees with deuterium distribution in the products, is discussed.

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