Synthesis of unsymmetrical biaryl ureas from N-carbamoylimidazoles: kinetics and application

T Rawling, AM McDonagh, B Tattam, M Murray

Index: Rawling, Tristan; McDonagh, Andrew M.; Tattam, Bruce; Murray, Michael Tetrahedron, 2012 , vol. 68, # 30 p. 6065 - 6070

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Citation Number: 10

Abstract

N-Carbamoylimidazoles dissociate in solution to yield imidazole and an isocyanate that may be reacted with another aryl amine to form an unsymmetrical biaryl urea. This paper investigates the reaction kinetics and the influence of electron withdrawing/donating substituents on the reaction of N-carbamoylimidazoles with aniline. The overall reaction mechanism involves two zwitterionic intermediates, formed during dissociation and upon ...