Preparation and ring transformation of isomeric β-lactam derivatives of bicyclic 1,3-thiazines

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Abstract

Ketene-imine cycloaddition reactions between cis- and trans-2-aryl-4a,5,6, 7,8,8a-hexahydro-4H-3,1-benzothazines and chloroacetyl chloride in the presence of base were investigated. Because of the diastereotopic CN faces of cyclohexane-condensed thiazines, both of the possible Staudinger addition product monochloro-β-lactam stereoisomers were obtained for both the cis and the trans compounds. The novel azetidin-2-ones were transformed into the corresponding 3-ethoxycarbonyl-2-aryl-1,5,5a,6,7,8,9,9a-octahydro-4,1- benzothiazepines with sodium ethoxide in a one-step procedure. Structural and stereochemical analyses of the synthesized compounds were carried out by means of IR and NMR spectroscopy.

Original languageEnglish
Pages (from-to)410-417
Number of pages8
JournalTetrahedron
Volume69
Issue number1
DOIs
Publication statusPublished - Jan 7 2013

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Keywords

  • Enamine
  • Ketene-imine cycloaddition
  • Ring transformation
  • Stereostructure and conformation determination by NMR including NOE
  • Thiazepine
  • Thiazine
  • β-Lactam isomers

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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