Access to 8-Aminoindolizine Fused with Quinone via Cu(OAc)2-Catalyzed Domino [4+2] Annulation

Abstract

Cu(OAc)2-catalyzed [4+2] annulation of N-substituted pyrrole-2-carbonitriles with quinones allowed access to a wide range of 8-aminoindolizines fused with quinones through a domino process involving intermolecular Michael addition, Thorpe-Ziegler type cyclization, and aromatization sequence. Biological evaluation of the resulting quinone-8-aminoindolizine hybrids revealed significant anticancer effects of these compounds in human hepatocellular cells (HepG2) and prostate adenocarcinoma cells (PC-3).