Indium-mediated one-pot benzimidazole synthesis from 2-nitroanilines or 1,2-dinitroarenes with orthoesters

One-pot reduction-triggered heterocyclizations from 2-nitroanilines or 1,2-dinitroarenes to benzimidazoles were investigated in this study. In the presence of indium/AcOH in ethyl acetate at reflux, reaction of 2-nitroanilines or 1,2-dinitroarenes with R-C(OMe)3 (R=Me, Ph) produced excellent yields of the corresponding benzimidazoles within 30 min to 6 h depending on the substituents of the starting materials. Indium-mediated heterocyclization of 2-nitroanilines to benzimidazole was faster and had better yields than 1,2-dinitroarenes to benzimidazole under similar reaction conditions.

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