SYNTHESIS OF 4- AND 7-QUINOLINESULFONAMIDES FROM 4,7-DICHLOROQUINOLINE

Action of sodium methanethiolate (in boiling DMF) towards 4,7-dichloroquinoline (1) or 7-ehloro-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) ox...

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Bibliographic Details
Published inHeterocycles Vol. 78; no. 1; pp. 93 - 101
Main Authors Marciniec, Krzysztof, Maslankiewicz, Andrzej
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
THIOLS
4-Quinolinone
Thioquinoline-Oxidative Chlorination
Quinolinesulfonamde
Nucleophilic Heteroaromatic Substitution
SULFONAMIDES
Quinolinesulfonyl Chloride
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Summary:Action of sodium methanethiolate (in boiling DMF) towards 4,7-dichloroquinoline (1) or 7-ehloro-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.
ISSN:0385-5414
DOI:10.3987/COM-08-11484