Mild and Direct Conversion of Quinoline N-Oxides to 2-Amidoquinolines with Primary Amides
A simple, one-pot procedure is described for the direct conversion of quinoline N-oxides to α-amidoquinolines with primary amides. This methodology is complimentary to the Abramovich reaction, which is limited to the introduction of secondary amides via imidoyl chlorides. Although reaction condition...
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Published in | Organic letters Vol. 8; no. 9; pp. 1929 - 1932 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
27.04.2006
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | A simple, one-pot procedure is described for the direct conversion of quinoline N-oxides to α-amidoquinolines with primary amides. This methodology is complimentary to the Abramovich reaction, which is limited to the introduction of secondary amides via imidoyl chlorides. Although reaction conditions are quite similar, omission of the base is key for successful reaction with primary amides, which were found not to proceed through the intermediacy of an imidoyl chloride but rather through an acyl isocyanate. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol060473w |