Copper-Catalyzed Domino Synthesis of Nitrogen Heterocycle-Fused Benzoimidazole and 1,2,4-Benzothiadiazine 1,1-Dioxide Derivatives

Abstract

A convenient copper-catalyzed domino method for the synthesis of nitrogen heterocycle-fused benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxides has been developed using readily available 2-bromo-<i>N</i>-phenylbenzenesulfonamides and benzimidazole derivatives as the starting materials. The domino process comprises an Ullmann-type <i>N</i>-arylation and intramolecular C–H amination. The inexpensive and efficient copper-catalyzed method should provide a new and useful strategy for for constructing novel, biologically interesting heterocycles containing benzoimidazole and 1,2,4-benzothiadiazine 1,1-dioxide motifs