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Palladium-catalyzed heteroannulation of 2-ARYL- 3-IODO-4-(Phenylamino)quinolines and 4-(N,N-allylphenylamino)-2-ARYL-3-iodoquinolines

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dc.contributor.advisor Mphahlele, M. J.
dc.contributor.author Lesenyeho, Lehlogonolo Godfrey
dc.date.accessioned 2011-02-01T10:51:50Z
dc.date.available 2011-02-01T10:51:50Z
dc.date.issued 2010-09
dc.identifier.citation Lesenyeho, Lehlogonolo Godfrey (2010) Palladium-catalyzed heteroannulation of 2-ARYL- 3-IODO-4-(Phenylamino)quinolines and 4-(N,N-allylphenylamino)-2-ARYL-3-iodoquinolines, University of South Africa, Pretoria, <http://hdl.handle.net/10500/3970> en
dc.identifier.uri http://hdl.handle.net/10500/3970
dc.description.abstract The previously described 2-aryl-4-chloro-3-iodoquinolines were prepared following literature procedure and in turn converted to the corresponding hitherto unknown 2-aryl-3-iodo-4-(phenylamino)quinoline derivatives using aniline in refluxing ethanol. These 2-aryl-3-iodo-4-(phenylamino)quinolines were reacted with allybromide in ethanol at room temperature to afford 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinoline derivatives. The 2-aryl-3-iodo-4-(phenylamino)quinoline and 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinoline derivatives were subjected to metal-catalysed carbon-carbon bond formations. Palladium(0)-copper iodide catalysed Sonogashira cross-coupling of 2-aryl-3-iodo-4-(phenylamino)quinoline with terminal alkynes afforded series of 1,2,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines in a single step operation. On the other hand, the 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinoline derivatives were found to undergo palladium-catalysed intramolecular Heck reaction to yield the corresponding 1,3,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines. All new compounds were characterized by using a combination of NMR (1H and 13C), IR, mass spectroscopic techniques as well as elemental analysis. en
dc.format.extent 1 online resource (viii, 124 leaves) : illustrations
dc.language.iso en en
dc.subject 2-Aryl-3-iodo-4-(phenylamino)quinoline en
dc.subject Sonogashira cross-coupling reaction en
dc.subject 4-(N,N-allylphenylamino)-2-aryl-3- iodoquinolines
dc.subject intramolecular Heck reaction
dc.subject 1H-pyrrolo[3,2-c]quinolines
dc.subject.ddc 547.2
dc.subject.lcsh Sonochemistry
dc.subject.lcsh Organic compounds -- Synthesis
dc.subject.lcsh Chemistry, Organic
dc.title Palladium-catalyzed heteroannulation of 2-ARYL- 3-IODO-4-(Phenylamino)quinolines and 4-(N,N-allylphenylamino)-2-ARYL-3-iodoquinolines en
dc.type Dissertation en
dc.description.department Chemistry
dc.description.degree M. Sc. (Chemistry)


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