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Paper | Regular issue | Vol 78, No. 1, 2009, pp.93-101
Published online, 25th August, 2008
DOI: 10.3987/COM-08-11484
■ Synthesis of 4- and 7-Quinolinesulfonamides from 4,7-Dichloroquinoline

Krzysztof Marciniec and Andrzej Maslankiewicz*

*Department of Organic Chemistry, The Medical University of Silesia, Jagiellonska 4, 41-200 Sosnowiec, Poland

Abstract

Action of sodium methanethiolate (in boiling DMF) towards 4,7-dichloroquinoline (1) or 7-chloro-1-methyl-4(1H)-quinolinone (11) occured via chlorine ipso-substitution followed by methanethiolato-S-demethylation to yield dithiolate 1A or thiolate 18A, which were: i) subjected to S-methylation, ii) oxidatively chlorinated to quinolinesulfonyl chlorides (5 or 14 and 15). Oxidative chlorination of 4,4’-bis (7-chloroquinolinyl) disulfide (7) led to 7-chloro-4-quinolinesulfonyl chloride (8). All quinolinesulfonyl chlorides 5, 8, 14 and 15 were effectively converted to corresponding azinesulfonamides 6, 9, 16 and 17.