Sequential Cu(II)-promoted oxidation/[3+2] cycloaddition/aromatization tandem reaction for the synthesis of 2-substituted benzo[f]isoindole-4,9-dione

摘要

An efficient method for the synthesis of 2-substituted benzo[f]isoindole-4,9-dione derivatives from N-substituted iminodiacetates and quinones via a Cu(II)-promoted oxidation/[3 + 2] cycloaddition/aromatization tandem reaction was reported. This tandem reaction uses a wide range of N-substituted iminodiacetate derivatives that contain the chain-alkyl, cycloalkyl, and aryl group on the N-atom. Based on optimized reaction conditions, the desired product of 2-substituted benzo[f]isoindole-4,9-diones was obtained in moderate to excellent yields. Taken together, the promising results of this research would provide an especially efficient strategy to synthesize polysubstituted pyrroles from easy available starting materials and promoted by cheaper Cu(OAc)(2).