One-pot synthesis of novel N,N-bis(isoxazol-5-yl)methyl tertiary arylamines via sequential diprop-3-ynylation and 1,3-dipolar cycloaddition from primary amines

Abstract

A simple and efficient one-pot multicomponent approach for the synthesis of tertiary arylamines bearing N,N-bis(isoxazol-5-yl)methyl groups is developed through reactions including sequential diprop-3-ynylation of primary amines with propargyl bromide in the presence of calcium hydride in N,N-dimethylformamide, and 1,3-dipolar cycloaddition with nitrile oxides generated in situ from hydroximyl chlorides in DMF-Et3N. This protocol provides advantages such as high regioselectivity, easy operation, and moderate-to-good product yields with a wide substrate scope under mild conditions.