Cycloaddition reactions of 1,3-benzothiazines-I. Reactions of 2-phenyl-4-H and 4-phenyl-2H-1,3-benzothiazine derivatives with substituted acetyl chlorides

L. Fodor, J. Szabó, P. Sohár

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

6,7-Dimethoxy-2-phenyl-4H-1,3-benzothiazine (1) and 6,7-dimethoxy-4-phenyl-2H-1,3-benzothiazine (2) react with substituted acetyl chlorides to give linearly, and new angularly condensed β-lactam derivatives (4,5). Heating of the latter compounds with hydrogen chloride in anhydrous ethanol leads to the formation of the corresponding 4H- and 2H-1,3-benzothiazinium chloride, respectively. The configurations of these compounds (the mutual positions of the substituents relative to the β-lactam ring) were determined by 1H and 13C studies, also making use of the aromatic solvent-induced shifts.

Original languageEnglish
Pages (from-to)963-966
Number of pages4
JournalTetrahedron
Volume37
Issue number5
DOIs
Publication statusPublished - 1981

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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