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: rbatey
chem.utoronto.ca
M. B. Bertrand, J. P. Wolfe, Tetrahedron, 2005, 61, 6447-6459.
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
