Carbamoylimidazolium salts as diversification reagents: an application to the synthesis of tertiary amides from carboxylic acids

An efficient method for the preparation of tertiary amides from carbamoylimidazolium salts and carboxylic acids is described. The transformation occurs at room temperature and under relatively mild conditions. The carbamoylimidazolium salts are obtained from the reaction of secondary amines with N,...

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Bibliographic Details
Published in:Tetrahedron letters 2003-09, Vol.44 (40), p.7485-7488
Main Authors: Grzyb, Justyna A., Batey, Robert A.
Format: Article
Language:English
Subjects:
amides
carbamoyl imidazolium salts
parallel synthesis
Weinreb amides
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Summary:An efficient method for the preparation of tertiary amides from carbamoylimidazolium salts and carboxylic acids is described. The transformation occurs at room temperature and under relatively mild conditions. The carbamoylimidazolium salts are obtained from the reaction of secondary amines with N, N′-carbonyldiimidazole, followed by methylation with methyl iodide. The utility of this reaction was demonstrated in the formation of Weinreb amides and in a short synthesis of fused bicyclic amides. The introduction of this reaction now permits carbamoylimidazolium salts to be utilized in the formation of tertiary amides, ureas, carbamates and thiocarbamates under a single set of conditions. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.08.026