Regio- and stereoselective α-halogenation of 2-aryl-1-methylsulfonyl-2,3-dihydroquinolin-4(1H)-ones

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 regios...

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Bibliographic Details
Published inSouth African journal of chemistry Vol. 54; no. 1; pp. 60 - 68
Main Authors Hlatshwayo, S.M., Fernandes, M.A., Mphahlele, M.J., Ndlovu, S.M.
Format Journal Article
LanguageEnglish
Published South African Chemical Institute (SACI) 21.05.2001
Subjects
Halogenation
Quinolones
Reseach articles
Stereochemistry
X-ray crystallography
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Summary: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.
ISSN:0379-4350