Copper(<scp>i</scp>)-catalyzed tandem synthesis of 2-acylquinolines from 2-ethynylanilines and glyoxals
Guanghui Wang, Jian Jia, Gang Liu, Mingwu Yu, Xiaoxiao Chu, Xiguang Liu, Ximei Zhao
Abstract
An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction of 2-ethynylanilines with glyoxals in the presence of piperidine has been developed. This new protocol successfully avoids multi-step operation and the use of highly toxic cyanides required in traditional methods, and provides a practical tool for synthetic and pharmaceutical chemists. Various 2-acylquinolines are obtained with perfect regioselectivity in moderate to good yields (up to 86%). The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.
Topics & Concepts
TandemRegioselectivityChemistryCombinatorial chemistryCatalysisPiperidineReaction conditionsOrganic chemistryMaterials scienceComposite materialCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques