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    Development of a Parallel Strategy for the Synthesis of a Library of 2-(3-Formyl-5-arylfuran-2-yl)ethylcarbamates from Dihydropyridinones

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    Issue Date
    2008-09-09
    Author
    Kim, An Na
    Publisher
    University of Kansas
    Format
    73 pages
    Type
    Thesis
    Degree Level
    M.S.
    Discipline
    Medicinal Chemistry
    Rights
    This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
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    Abstract
    2,3-Dihydropyridin-4(1H)-ones were utilized as scaffolds for the syntheses of libraries of 5-arylethynyl-2,3-dihydropyridin-4(1H)-ones and 2-(3-formyl-5-arylfuran-2-yl)ethylcarbamates. 2,3-Dihydropyridin-4(1H)-ones were prepared from piperidones, ynones, and pyridones and used for the synthesis of a library of 5-arylethynyl-2,3-dihydropyridin-4(1H)-ones employing a Sonogashira reaction. Further reaction of these compounds using an Au(III)-catalyzed cyclization method yielded formylfurans. N-Boc and N-benzyl protected 2,3-dihydropyridin-4(1H)-ones were prepared for the Sonogashira reaction. N-Boc-protected 5-iodo-2,3-dihydropyridin-4(1H)-ones provided tert-butyl 5-arylethynyl-4-oxo-3,4-dihydropyridine-1(2H)-carboxylates in moderate to excellent yields while the N-Bn-protected enaminones provided low yields of 5-arylethynyl-1-benzyl-2,3-dihydropyridin-4(1H)-ones. Furan formation was achieved by Au(III)-catalyzed and Cu-mediated cyclizations. (±)tert-Butyl 1-(3-formyl-5-phenylfuran-2-yl)propan-2-ylcarbamates were obtained during the Sonogashira reactions catalyzed by Cu(I), while (±)tert-Butyl 1-(3-formyl-5-phenylfuran-2-yl)-3-phenylpropan-2-ylcarbamates were formed by the Au(III)-catalyzed cyclization. A library of 16 compounds of highly substituted furans was synthesized in moderate to excellent yields.
    URI
    http://hdl.handle.net/1808/4335
    Collections
    • Medicinal Chemistry Dissertations and Theses [80]
    • Theses [3906]

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    785-864-8983
    KU Libraries
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    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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