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Development of a copper-catalyzed amidation-base-promoted cyclization sequence for the synthesis of 2-aryl- and 2-vinyl1-4 quinolones

Author(s)
Jones, Carrie Preston
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Massachusetts Institute of Technology. Dept. of Chemistry.
Advisor
Stephen L. Buchwald.
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M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. http://dspace.mit.edu/handle/1721.1/7582
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Abstract
A direct two-step method for the preparation of 2-aryl- and 2-vinyl-4-quinolones that utilizes a copper-catalyzed amidation of ortho-halophenones followed by a base-promoted Camps cyclization of the resulting N-(2-keto-aryl)amides is described. With Cul, 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 using the conditions that are described.
Description
Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2007.
 
Vita.
 
Includes bibliographical references (p. 45-48).
 
Date issued
2007
URI
http://hdl.handle.net/1721.1/41771
Department
Massachusetts Institute of Technology. Department of Chemistry
Publisher
Massachusetts Institute of Technology
Keywords
Chemistry.

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