Chemoselective Synthesis of Tetrahydropyrimidines and Dihydropyrrolidones through Three-Component Reaction of Amines, 1,3,5-Triazinanes, and Alkyne Esters

Abstract

A three-component reaction of amines, 1,3,5-triazinanes, and alkyne esters for the construction of tetrahydropyrimidines and dihydropyrrolidones derivatives was reported. Shifting the substituent group of 1,3,5-triazinanes led to the chemoselective synthesis. As three-atom synthons, aryl substituted 1,3,5-triazinanes were applied to the regioselective synthesis of tetrahydropyrimidines. Alkyl substituted 1,3,5-triazinanes working as two-atom synthons promoted intramolecular cyclization to generate dihydropyrrolidones analogues. The practicality of the developed methods was demonstrated by easy operation, catalyst-free conditions, and good functional groups tolerance.