Trisubstituted ureas can be synthesized in a one-pot fashion from bench-stable a-chloroaldoxime Omethanesulfonates and secondary amines under mild reaction conditions. Two practical protocols have been developed to achieve various urea syntheses from both secondary aromatic amines and aliphatic amines.Scheme 1 Rearrangement of a-chloroaldoxime Omethanesulfonates.
One-Pot Synthesis of Trisubstituted Ureas from -Chloroaldoxime O-Methanesulfonates and Secondary Amines. -The reaction proceeds via intermediary isocyanates generated by Tiemann-type rearrangement of -chloroaldoxime mesylates in the presence of water and a base. -(KAEOBAMRUNG*, J.; LANUI, A.; MAHAWONG, S.; DUANGMAK, W.; RUKACHAISIRIKUL, V.; RSC Adv. 5 (2015) 72, 58587-58594, http://dx.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.