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Thermolytic ring closure reactions of 4-azido-3-phenylsulfanyl-and 4-azido-3-phenylsulfonyl-2-quinolones to 12H-quinolino-[3,4-b][1,4]benzothiazin-6(5H)-ones

✍ Scribed by Anna E. Täubl; Klaus Langhans; Thomas Kappe; Wolfgang Stadlbauer

Publisher: Journal of Heterocyclic Chemistry
Year: 2002
Tongue: English
Weight: 61 KB
Volume: 39
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570390621

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✦ Synopsis

Abstract

4‐Hydroxy‐3‐phenylsulfanyl‐2‐quinolones 2 and 4‐hydroxy‐3‐sulfonyl‐2‐quinolones 7, which are readily accessible from 4‐hydroxy‐2‐quinolones 1 and diphenyldisulfide or thiophenol, can be converted to 4‐azido‐3‐phenylsulfanyl‐2‐quinolones 10 or 4‐azido‐3‐phenylsulfonyl‐2‐quinolones 12 via 4‐chloro‐3‐phenylsul‐fanyl‐2‐quinolones 5 or 4‐chloro‐3‐phenylsulfonyl‐2‐quinolones 9, respectively. Thermolysis of the azides 10 and 12 results in a cyclization reaction to give quinolino[3,4‐b][1,4]benzothiazinone 11 and quino‐lino[3,4‐b][1,4]benzothiazinone dioxides 13, respectively. The conditions for thermolysis have been studied by differential scanning calorimetry (DSC).

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