Cycloaddition reactions of 1,3-benzothiazines - 6. Reactions of 1,3-benzothiazine derivatives with substituted acetyl chlorides

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Abstract

6, 7-Dimethoxy-2H-l,3-benzothiazine derivatives (1, 8) react with substituted acetyl chlorides to give angularly condensed β -lactams (3a-d, 10, 11). The cis compound 11 was epimerised to the trans derivative 12. From the interaction of 2-phenyl-6,7-dimethoxy-4H-1,3-benzothiazine (7) and α -chloro-phenylacetyl chloride two stereoisomeric β -lactam derivatives (9a, b) were isolated, whereas in the other cases studied the reactions leading to β -lactams proved to be stereospecific. Analogous reactions of 4-methyl-6,7-dimethoxy-2H-l,3-benzothiazine (5) furnished the enamides 6a,c, d. Structures of the new compounds and configurations of the diastereomers were elucidated by IR and NMR spectroscopy.

Original languageEnglish
Pages (from-to)4387-4393
Number of pages7
JournalTetrahedron
Volume40
Issue number21
DOIs
Publication statusPublished - 1984

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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