Synthesis and structural characterisation of 927 4H-1,3-benzothiazine derivatives

L. Fodor, G. Bernáth, Jari Sinkkonen, Kalevi Pihlaja

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Abstract

The ring-closure reactions of N-arylthiomethylaroylamide derivatives (1a-g) in the presence of phosphorus oxychloride gave 2-aryl-4H-1,3-benzo-thiazines (2a-g). 2-(3-Chlorophenyl)-6-methyl-4H-1,3-benzothiazine (2b) was reduced with Zn to obtain the corresponding 2,3-dihydro derivative (3b). Potassium permanganate oxidation of 2-(4-chlorophenyl)-2,3-diethoxy-4H- (2e) and 2-(2-fluorophenyl)-6,7-diethoxy-4H-1,3-benzo-thiazines (2g) gave the corresponding 4-ones (4e,g). The reactions of 2-(4-chlorophenyl)-6-methyl-4H-1,3-benzothiazine (2c) with substituted acetyl chlorides led to linearly condensed β-lactams (5a,b). The structures of the compounds studied were confirmed by 1H and 13C NMR and by their characteristic mass spectrometric fragmentations.

Original languageEnglish
Pages (from-to)927-931
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume39
Issue number5
Publication statusPublished - Sep 2002

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Thiazines
Potassium Permanganate
Derivatives
Lactams
Nuclear magnetic resonance
Oxidation

ASJC Scopus subject areas

  • Organic Chemistry

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Synthesis and structural characterisation of 927 4H-1,3-benzothiazine derivatives. / Fodor, L.; Bernáth, G.; Sinkkonen, Jari; Pihlaja, Kalevi.

In: Journal of Heterocyclic Chemistry, Vol. 39, No. 5, 09.2002, p. 927-931.

Research output: Contribution to journalArticle

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