Synthesis of Stable N–H Imines with a Benzo[7,8]indolizine Core and Benzo[7,8]indolizino[1,2-<i>c</i>]quinolines via Copper-Catalyzed Annulation of α,β-Unsaturated <i>O</i>-Acyl Ketoximes with Isoquinolinium <i>N</i>-Ylides
Chun‐Bao Miao, Xiao-Qi Qiang, Xiaoli Xu, Xiaoqing Song, Su-Qing Zhou, Xinyu Lyu, Hai‐Tao Yang
Abstract
A copper-catalyzed annulation of α,β-unsaturated O-acyl ketoximes with isoquinolinium N-ylides has been developed for the concise synthesis of stable N–H imines with a benzo[7,8]indolizine core. When β-(2-bromoaryl)-α,β-unsaturated O-acyl ketoximes are used as the starting materials, a cascade cyclization occurs to afford the benzo[7,8]indolizino[1,2-c]quinolines.
Topics & Concepts
ChemistryIndolizineAnnulationCatalysisMedicinal chemistryCopperStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions