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Synfacts 2009(5): 0482-0482  
DOI: 10.1055/s-0029-1216614
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Carbonylative Synthesis of 2-Quinolones

Contributor(s): Victor Snieckus, Jignesh P. Patel
A. C. Tadd, A. Matsuno, M. R. Fielding, M. C. Willis*
University of Oxford and AstraZeneca Process Research and Development, Macclesfield, UK
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

A highly selective and efficient ­palladium-catalyzed synthesis of 2-quinolones from 2-(2-haloalkenyl)aryl halides via an intermolecular aminocarbonylation under CO atmosphere followed by intramolecular amidation sequence is reported. One example of an isoquinolone is ­reported from the same substrate simply by delaying the introduction of CO to allow the intermolecular amidation first followed by carbonylation sequence. One example of an azaquinolone is reported in good yield (73%).