2026-09-18T20:33:26Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/417712022-01-13T07:54:21Zcom_1721.1_7582com_1721.1_7581col_1721.1_131023
Stephen L. Buchwald.
Jones, Carrie Preston
Massachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2008-05-19T16:16:19Z
2008-05-19T16:16:19Z
2007
2007
http://hdl.handle.net/1721.1/41771
226299458
Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2007.
Vita.
Includes bibliographical references (p. 45-48).
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.
by Carrie Preston Jones.
S.M.
69 p.
eng
Massachusetts Institute of Technology
M.I.T. theses are protected by
copyright. They may be viewed from this source for any purpose, but
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http://dspace.mit.edu/handle/1721.1/7582
Chemistry.
Development of a copper-catalyzed amidation-base-promoted cyclization sequence for the synthesis of 2-aryl- and 2-vinyl1-4 quinolones
Thesis
application/pdf
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Publication
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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.</Abstract>
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