Copper-Catalyzed Cycloadditions of Diazo Compounds with Imidazolidines/Hexahydropyrimidines for the Syntheses of N-Heterocycles.

Abstract

Reported herein are the unprecedented copper-catalyzed formal [n + 1]/[n + 3] (n = 5, 6) cycloadditions of diazo compounds with imidazolidines/hexahydropyrimidines, thus providing a general, economical, and efficient route to construct different sized (six- to nine-membered) diaza-heterocycles in moderate to excellent yields under mild reaction conditions. This strategy features the use of copper catalyst to accomplish such diverse annulations and the utilization of imidazolidines/hexahydropyrimidines as stable 1,5-/1,6-dipoles.