Synthesis of quinoline analogues

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dc.contributor.advisor Sammelson, Robert E. Abu Alnjaa, Alaa Mohammad 2013-12-19T17:14:47Z 2013-12-14 2013-12-14
dc.description.abstract Quinoline is an important class of nitrogen compounds containing aromatic heterocycle. Lavendamycin and streptonigrin are known antibiotic, antitumor agents which contain the quinoline-5,8-dione functional group that provide their antitumor properties. Quinonline-5,8- diones are an important class of compounds because of their wide spectrum of biological activities. Most cancer cells show an elevated level of NQO1 enzyme which activates lavendamycin to act as an antitumor agent. Lavendamycin contains a β-carboline which has a substituted pyridine connected to the 2-position of the quinolone-5,8-dione. The research goal is to study various synthetic methods and reactions to produce 2-chloro-8-hydroxy-5,7-dinitroquinoline and 8-methoxyquinoline analogues. In order to approach this, 8-hydroxyquinoline goes through three or four synthetic steps to install the chloro group at the two position of the quinoline ring. Oxidation of 8- hydroxyquinoline to produce 8-hydroxyquinoline-N-oxide, reaction with acetic anhydride to give 8-acetoxy-2-hydroxyquinoline is followed by conversion into 2-chloro-8-hydroxyquinoline with POCl3. Finally, nitration provides 2-chloro-8-hydroxy-5,7-dinitroquinoline. The 8-hydroxy derivatives can be converted to 8-methoxyquinoline analogues with methyl iodide and potassium carbonate. en_US
dc.description.sponsorship Department of Chemistry
dc.description.tableofcontents Introduction and background literature -- Synthesis of 8-hydroxyquinoline and 8-methoxyquinoline derivatives.
dc.subject.lcsh Quinoline -- Derivatives -- Synthesis.
dc.title Synthesis of quinoline analogues en_US
dc.type Research paper (M.A.), 3 hrs. Thesis (M.A.) en_US 2016-12-14 2016-12-14

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  • Research Papers [5100]
    Research papers submitted to the Graduate School by Ball State University master's degree candidates in partial fulfillment of degree requirements.

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