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Synthesis and transformation of the 2,6,8-triaryl-2,3-dihydroquinolin-4(1H)-ones

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dc.contributor.advisor Mphahlele, M.J. Oyeyiola, Felix Adetunji 2012-06-25T08:15:30Z 2012-06-25T08:15:30Z 2011-11
dc.identifier.citation Oyeyiola, Felix Adetunji (2011) Synthesis and transformation of the 2,6,8-triaryl-2,3-dihydroquinolin-4(1H)-ones, University of South Africa, Pretoria, <> en
dc.description.abstract The 2-aryl-2,3-dihydroquinolin-4(1H)-ones were prepared via acid-catalyzed cyclization of the corresponding 2-aminochalcones, which were in turn, prepared by base-promoted Claisen-Schmidt aldol condensation of 2-aminoacetophenone and benzaldehyde derivatives. The 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones were prepared by reacting 2-aryl-2,3-dihydroquinolin-4(1H)-ones with N-bromosuccinimide (NBS) in carbon tetrachloride-chloroform mixture at room temperature. The 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones were subjected to palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with arylboronic acid using dichlorobis(triphenylphosphine)palladium(II)-tricycohexylphosphine as catalyst mixture and potassium carbonate as a base in dioxane-water under reflux to afford the corresponding novel 2,6,8-triaryl-2,3-dihydroquinolin-4(1H)-ones in a single-pot operation. The latter were subjected to thallium(III) p-tolylsulfonate in dimethoxyethane under reflux to yield the 2,6,8-triarylquinolin-4(1H)-ones. The 2,6,8-triaryl-2,3-dihydroquinolin-4(1H)-ones were treated with molecular iodine in refluxing methanol to afford the corresponding 2,6,8-triaryl-4-methoxyquinolines. All the new compounds were characterized using a combination of 1H NMR & 13C NMR spectroscopy, IR and mass spectroscopic techniques. en
dc.format.extent 1 online resource (ix, 99 leaves)
dc.language.iso en en
dc.subject 2-aminochalcones en
dc.subject Cross-coupling reaction en
dc.subject Suzuki-Miyaura en
dc.subject.ddc 547.2
dc.subject.lcsh Organic compounds -- Synthesis
dc.subject.lcsh Pharmaceutical chemistry
dc.title Synthesis and transformation of the 2,6,8-triaryl-2,3-dihydroquinolin-4(1H)-ones en
dc.type Dissertation en
dc.description.department Chemistry M.Sc. (Chemistry)

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