An unexpected isomerization of 1,3-benzothiazine and isoquinoline-condensed β-lactams

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7 Citations (Scopus)

Abstract

A series of novel aryl-substituted β-lactams condensed with 1,3-benzothiazines, isoquinolines or 1,4-benzothiazepine were obtained by means of the Staudinger reaction and isomerized in the presence of sodium methoxide to the thermodynamically more stable form. The structures of the new molecules were determined by NMR spectroscopy. Theoretical calculations corroborate the experimentally observed structure-reactivity relationships.

Original languageEnglish
Pages (from-to)54-61
Number of pages8
JournalJournal of Molecular Structure
Volume983
Issue number1-3
DOIs
Publication statusPublished - Nov 1 2010

Keywords

  • Cis-trans-β-lactams
  • DFT analysis
  • Isoquinoline
  • NMR spectroscopy
  • Staudinger reaction
  • Sulfur nitrogen heterocycles

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

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