Copper(i)-catalyzed tandem synthesis of 2-acylquinolines from 2-ethynylanilines and glyoxals

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.

Automated summary

An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction has been developed, providing a practical tool for synthetic and pharmaceutical chemists. The method avoids multi-step operation and the use of highly toxic cyanides, with various products obtained with perfect regioselectivity in moderate to good yields. The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.