Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 21, Pages 7968-7973Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo701384n
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Funding
- NIGMS NIH HHS [GM 1S10RR13886-01, GM 58160] Funding Source: Medline
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A direct two-step method for the preparation of 2-aryl- and 2-vinyl-4-quinolones that utilizes a copper-catalyzed amidation of o-halophenones followed by a base-promoted Camps cyclization of the resulting N-(2-ketoaryl)amides is described. With CuI, a diamine ligand, and base as the catalyst system, the amidation reactions proceed in good yields for a range of aryl, heteroaryl, and vinyl amides. The subsequent Camps cyclization efficiently provides the desired 4-quinolones with the conditions that are described.
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