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Feb 24, 2004Article Details
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Regio- and Stereoselective a-Halogenation of 2-Aryl-1-methylsulfonyl-2,3- dihydroquinolin-4(1H)-ones
Abstract
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.
South African Journal of Chemistry Vol.54 2001: 60-68
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