Cyanomethylative cyclization of unactivated alkenes with nitriles for the synthesis of cyano-containing ring-fused quinazolin-4(3H)-ones

Abstract

The synthesis of cyano-containing ring-fused quinazolin-4(3H)-one derivatives was developed under metal-free conditions. This synthesis involves radical C(sp³)–H functionalization of alkyl nitriles, and cascade radical addition/cyclization with N-alkylated quinazolinones to deliver cyanoalkylated pyrrolo- and piperidino-quinazolin-4(3H)-ones in moderate to excellent yields. Moreover, a derivative of the natural product leucomidine C was synthesized conveniently using the current protocol.