oa South African Journal of Chemistry - Regio- and stereoselective α-halogenation of 2-aryl-1-methylsulfonyl-2,3-dihydroquinolin-4(1H)-ones
|Article Title||Regio- and stereoselective α-halogenation of 2-aryl-1-methylsulfonyl-2,3-dihydroquinolin-4(1H)-ones|
|© Publisher:||South African Chemical Institute (SACI)|
|Journal||South African Journal of Chemistry|
|Author||M.J. Mphahlele, S.M. Hlatshwayo, S.M. Ndlovu and M.A. Fernandes|
|Publication Date||Jan 2001|
|Pages||60 - 68|
|Keyword(s)||Halogenation, Quinolones, Reseach articles, Stereochemistry and X-ray crystallography|
2-Aryl-1-methylsulfonyl-2,3-dihydroquinolin-4(1H)-ones are readily converted into the corresponding 2-aryl-3-iodo- and 2-aryl-3-bromo-1-methylsulfonyl-2,3-dihydroquinolin-4(1H)-ones using iodine in methanol and pyridinium perbromide in acetic acid, respectively. The reactions were found to be regioselective and stereoselective by 1H NMR spectroscopy, affording in all cases the 2,3-trans isomers. X-ray crystallography was also used to investigate the relative stereochemistry of these 3-halo derivatives.
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