Synthesis of Indenone-Fused Pyran Derivatives from Aryl Enaminones and Cyclopropenones through Unsymmetrical Relay C-H Bond Activation and Double C-C/C-O Bond Formation.

Abstract

Presented herein is a novel synthesis of indenone-fused pyran derivatives via the cascade reactions of aryl enaminones with cyclopropenones. The formation of products involves a one-pot cascade procedure consisting of aryl C-H bond and enamine C-H bond functionalization along with C-C bond cleavage of cyclopropenone and 1,3-rearrangement of the in situ-formed allylic alcohol moiety followed by intramolecular O-nucleophilic addition and Me2NH elimination. To our knowledge, this is the first synthesis of indenone-fused pyran derivatives via simultaneous formation of both indenone and pyran scaffolds through concurrent unsymmetrical relay C-H bond activation and double C-C/C-O bond formation. Moreover, the usefulness of this method is further showcased by its suitability for large-scale synthetic scenarios and diverse transformations of products.