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

Justyna A. Grzyb, Ming Shen, Chiaki Yoshina-Ishii, W. Chi, R. Stanley Brown and Robert A. Batey*

*Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ont., Canada M5S 3H6, Email: rbateychem.utoronto.ca

J. A. Grzyb, M. Shen, C. Yoshina-Ishii, W. Chi, R. S. Brown, R. A. Batey, Tetrahedron, 2005, 61, 7153-7175.

DOI: 10.1016/j.tet.2005.05.056


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Abstract

Readily prepared carbamoylimidazolium salts act as efficient N,N-disubstituted carbamoylating reagents, as a result of the ‘imidazolium' effect. The salts react with amines, thiols, phenols/alcohols, and carboxylic acids in high yields, without the need for subsequent chromatographic purification of the products, producing ureas, thiocarbamates, carbamates, and amides, respectively.

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Key Words

carbamoylimidazolium salts, thiocarbamoylimidazolium salts, ureas, thioureas, carbamates, thiocarbamates, amides


ID: J72-Y2005-2990