Indoles Oxidative Ring-Opening/Cyclization Cascade with the 1,2-Diaminoarenes: Direct Synthesis of 2-Aryl-3-(2-aminoaryl)quinoxalines.

A mild oxidative sequential tandem reaction was developed to rapidly generate 2-aryl-3-(2-aminoaryl) quinoxalines. This method exploited 2-substituted indoles as substrate to form quinoxalines in a one-pot reaction. The key to this tandem reaction was the formation of 3-iodoindoles, which underwent Kornblum-type oxidation with DMSO to generate active imine 2-substitued 3H-indol-3-ones. The active imines were captured in situ by 1,2-diaminobenzenes to construct diverse quinoxalines. The transformation can be accomplished at room temperature with excellent functional group tolerance.