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    Palladium-phosphinous acid-catalyzed carbon-carbon and carbon-heteroatom bond formation and synthesis of new antimalarial drugs

    Cover for Palladium-phosphinous acid-catalyzed carbon-carbon and carbon-heteroatom bond
      formation and synthesis of new antimalarial drugs
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    View/Open: ekoue-koviKekeli.pdf (2.0MB) Bookview

    Creator
    Ekoue-Kovi, Kekeli Adjoa Sika.
    Description
    Thesis (Ph.D.)--Georgetown University, 2008.; Includes bibliographical references. Palladium-catalyzed carbon-carbon and carbon-heteroatom bond forming reactions have gained increased importance in organic transformations. Palladium-phosphinous acids and chlorophosphines have proved to be useful in cross-coupling reactions due to their high catalytic activity and to their stability to air and moisture. In this thesis, it is reported that palladium-phosphinous acids can catalyze the Suzuki coupling reactions of aryl and acyl chlorides to afford biaryls and ketones in high yields. Since palladium-phosphinous acids proved useful for oxidative esterification of aldehydes, a similar one-pot procedure generating amides was developed. Moreover, new alkylarylphosphinous acids exhibiting a naphthyl, a biphenyl or a 2,6-dimethylphenyl group were synthesized and applied to transition metal-catalyzed cross-coupling reactions. The spread of chloroquine (CQ) resistant malaria strains has led to the development of new heme-targeted antimalarials. It has been established that the pharmacophore of CQ consists of a terminal dialkylamino side chain as well as a 7-chloroquinolyl ring. The basic CQ side chain and the quinolyl N are known facilitate the accumulation of the drug in the digestive vacuole of the malaria parasite. In an attempt to find CQ analogues that are effective against both chloroquine resistant (CQR) and chloroquine sensitive (CQS) strains of the malaria parasite, a series of 4N and 4O chloroquine derivatives exhibiting different side chain structures and CQ amides were prepared and tested. Some of these compounds exhibit better antimalarial activity over CQ.
    Permanent Link
    http://hdl.handle.net/10822/552879
    Date Published
    2008
    Subject
    Chemistry, Organic
    Type
    thesis
    Publisher
    Georgetown University
    Collections
    • Graduate Theses and Dissertations - Chemistry
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      Xu, Hanhui (Georgetown University, 2012)
      Palladium-phosphinous acids and chlorophosphine analogues have attracted increasing interest due to their high catalytic activity in various organic transformations, long shelf-life and facile handling. In this thesis, it ...
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    Georgetown University Seal
    ©2009 - 2023 Georgetown University Library
    37th & O Streets NW
    Washington DC 20057-1174
    202.687.7385
    digitalscholarship@georgetown.edu
    Accessibility