The main objective of this investigation was to study palladium-catalyzed coupling of
2-aryl-4-chloro-3-iodoquinolines with phenyl boronic acid in order to assess the
regioselectivity of carbon-carbon bond formation at either C3 or C4. The 2-aryl-4-
chloro-3-iodoquinolines were subjected to Pd(PPh3)4-catalyzed coupling reaction
with phenyl boronic acid in DMF in the presence of 2M sodium carbonate (aq) to
afford 2,3-diaryl-4-chloroquinolines. Reaction of 2,3-diaryl-4-chloroquinolines with
sodium methoxide in MeOH-DMF mixture under reflux afforded the corresponding
2,3-diaryl-4-methoxyquinoline. An alternative route to the latter involving palladiumcatalyzed
cross-coupling reaction of 2-aryl-3-iodo-4-methoxyquinolines derived from
the reaction of 2-aryl-4-chloro-3-iodoquinolines with sodium methoxide in refluxing
methanol-THF mixture was also investigated. The 2,3-diaryl-4-methoxyquinolines
were subjected to further studies of chemical transformation with boron tribromide to
afford the corresponding 2,3-diarylquinolin-4(1H)-ones. All new compounds were
characterized using a combination of NMR (1H and 13C), IR and mass spectroscopic
techniques as well as elemental analysis. / Chemistry / M. Sc. (Chemistry)
| Identifer | oai:union.ndltd.org:netd.ac.za/oai:union.ndltd.org:unisa/oai:uir.unisa.ac.za:10500/2275 |
| Date | 31 May 2008 |
| Creators | Mtshemla, Vathiswa |
| Contributors | Mphahlele, M.J. (Prof.) |
| Source Sets | South African National ETD Portal |
| Language | English |
| Detected Language | English |
| Type | Dissertation |
| Format | 1 online resource (vii, 77 leaves : ill.) |
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