A mild and efficient synthesis of N-aryl glycines by the rearrangement of 2-chloro-N-aryl acetamides

Abstract

A mild and efficient one-pot procedure was developed for the synthesis of substituted N-aryl glycines from 2-chloro-N-aryl acetamides by intermolecular cyclization in the presence of CuCl₂·2H₂O and KOH under reflux condition in acetonitrile medium. The reaction mechanism substantiates the formation of the intermediate 1,4-diarylpiperazine-2,5-dione, which on cleaving with ethanolic KOH afforded the desired products in high yields and in short durations. Both electron-donating and electron-withdrawing substituents on the aromatic rings were well tolerated.