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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Bibliographic Details
Published inOrganic letters Vol. 8; no. 9; pp. 1929 - 1932
Main Authors Couturier, Michel, Caron, Laurence, Tumidajski, Stephanie, Jones, Kris, White, Timothy D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.04.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRIPLEX FORMATION
DESIGN
ADENOSINE RECEPTOR ANTAGONISTS
RECOGNITION
DNA
PYRIDINE 1-OXIDES
CHLORIDES
INHIBITORS
DIRECT ACYLAMINATION
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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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ISSN:1523-7060
1523-7052
DOI:10.1021/ol060473w