Transition-Metal-Free Cross-Dehydrogenative Couplings of 8-Aminoquinoline Amides at C5 Position with Acetonitrile, Ethers or Acetone

A novel and efficient method for highly regioselective cyanomethylation of 8-aminoquinoline amides at C5 position was developed. Such reactions proceed under transition metal-free and base-free conditions. This protocol features simple operation, high efficiency, good functional group tolerance and broad substrate scope. Moreover, the etherification or acetonation products were also obtained when acetonitrile was replaced by ethers or acetone, and a radical process was involved in the reaction.

Automated summary

A novel and efficient method has been developed for highly regioselective cyanomethylation of 8-aminoquinoline amides at the C5 position, under transition metal-free and base-free conditions. This protocol offers simple operation, high efficiency, good functional group tolerance, and broad substrate scope. Additionally, etherification or acetonation products can be obtained when acetonitrile is replaced by ethers or acetone, with a radical process involved in the reaction.