Ph<inf>3</inf>P/I<inf>2</inf>-mediated synthesis of N,N′,N″-substituted guanidines and 2-iminoimidazolin-4-ones from aryl isothiocyanates

Abstract

© 2017 American Chemical Society. A convenient one-pot procedure for the synthesis of acyclic and cyclic guanidines mediated by the Ph3P/I2system is described. Sequential condensation of aryl isothiocyanates with amines followed by dehydrosulfurization and guanylation could lead to both symmetric and unsymmetric N,N′,N″-substituted derivatives. Through a tandem guanylation-cyclization, a series of 2-iminoimidazolin-4-ones could also be prepared in good yields from the reaction of aryl isothiocyanates with amino acid methyl esters.