Investigation of ring transformations of diaryl-β-lactams condensed with 1,3-benzothiazines

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Abstract

Reactions of derivatives of the isoquinoline analog trans-2,2a-diaryl-2,2a- dihydro-5,6- dimethoxy-1H,8H-azeto[2,1-b][1,3]benzothiazin-1-one were studied under basic conditions. Their treatment with sodium methoxide in methanol resulted first in alcoholysis of the β-lactam ring, followed by opening of the thiazine ring and oxidation of the thiol moiety to disulfide. Thus, the corresponding β-amino acid derivatives, disulfides of N-(ortho- mercaptobenzyl)- substituted diaryl-3-aminoacrylic acid methyl esters, were obtained in good yields. The structures of the new molecules were proved by means of NMR and IR spectroscopy. Geometric isomerism investigations indicated the presence of the Z forms of the acrylic acid moiety.

Original languageEnglish
Pages (from-to)37-46
Number of pages10
JournalArkivoc
Volume2012
Issue number5
DOIs
Publication statusPublished - 2012

Keywords

  • 1 3-Benzothiazine
  • 3-aminoacrylic acid
  • Aring opening
  • Disulfide
  • β-amino acid
  • β-lactam

ASJC Scopus subject areas

  • Organic Chemistry

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