Unprecedented Intermolecular Transamidation Reaction of N-Carbamoylmethyl-N′-tosylguanidines

Abstract

(Matrix presented) N-Carbamoylmethyl-N′-tosyl guanidine 2 reacts easily with primary alkylamines to afford substituted carboxamides 3. The reaction proceeds via a five-membered-ring intermediate 5, which could be isolated, and features a rare example of an intermolecular transamidation reaction under mild conditions.