Copper-catalyzed synthesis of aminoquinolines from β-(2-aminophenyl)-α,β-ynones using DMF as dual synthon

Abstract

A new and efficient method has been developed for the synthesis of 4-aminoquinoline through aerobic Cu(I)-catalyzed cyclization of β-(2-aminophenyl)-α,β-ynones. Under the optimized conditions, DMF could serve as a methine source to introduce C2 carbon and a nitrogen source to incorporate amino functionality in the 4^th position. Mechanistic studies using ¹³C- and DMF-d₇ revealed that the methine group was derived from a methyl substituent.