A Mild Method for the Synthesis of Carbamate-Protected Guanidines Using the Burgess Reagent

Abstract

A simple method for the synthesis of carbamate-protected guanidines from primary amines is described. A variety of thioureas derived from primary amines and isothiocyanates react with the Burgess reagent to give the corresponding guanidines via either a stepwise or one-pot procedure. By tuning the carbamoyl units of isothiocyanates and the Burgess reagent, differentially <i>N,N′</i>-diprotected guanidines can be obtained. Selective deprotection of the products affords <i>N-</i>monoprotected guanidines