Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles

Abstract

A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides. The reaction pathway involves Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm rearrangement and an oxo-Diels–Alder reaction sequence, resulting in continuous multiple bond-forming events including C–N, C–O and C–H bonds to rapidly build up molecular complexity.