Access to pyrrolo[2,1-a]isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations

Abstract

A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C–C & C–N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N–O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.