Tetrahedron

Carbamoylimidazolium and thiocarbamoylimidazolium salts: novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides

JA Grzyb, M Shen, C Yoshina-Ishii, W Chi, RS Brown…

Index: Grzyb, Justyna A.; Shen, Ming; Yoshina-Ishii, Chiaki; Chi; Brown, R. Stanley; Batey, Robert A. Tetrahedron, 2005 , vol. 61, # 30 p. 7153 - 7175

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Citation Number: 91

Abstract

Carbamoylimidazolium salts act as efficient N, N-disubstituted carbamoylating reagents. These salts are readily prepared by the sequential treatment of secondary amines with N, N′-carbonyldiimidazole (CDI) and iodomethane. The carbamoylimidazolium salts are more efficient carbamoyl transfer reagents than the intermediate carbamoylimidazoles, as a result of the 'imidazolium'effect. Kinetic studies on the base promoted hydrolysis of both ...

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