A Synthesis of Functionalized Benzimidazoles via the Three-Component Reaction of Terminal Alkynes, Phenylsulfonyl Azide, and Phenylenediamine-1,3-dicarbonyl Adducts

Abstract

Functionalized benzimidazoles are produced through a three-component reaction that combines phenylenediamine-1,3-dicarbonyl adducts, terminal alkynes, and phenylsulfonyl azide. This synthesis involves the generation of N-sulfonylketenimine intermediates via a copper-catalyzed azide-alkyne cycloaddition, which is subsequently followed by cyclization with the phenylenediamine-1,3-dicarbonyl adducts. The method is noted for its efficiency and versatility across a range of substrates, with the final compound’s structure being validated through single-crystal X-ray analysis.

Keywords

Benzimidazole - N-Heterocycles - 1,2-Diaminibenzene - 1,3-Dicarbonyls - N-Sulfonylketenimine

• References

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