Novel indole syntheses by ring transformation of β-lactam-condensed 1,3-benzothiazines into indolo[2,3-b][1,4]benzothiazepines and indolo[3,2-c]isoquinolines

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10 Citations (Scopus)

Abstract

ortho-Nitrophenyl-substituted condensed 1,3-benzothiazines proved to be a useful core unit in indole syntheses under non-reductive conditions. Thus, the treatment of ortho-nitro-2-aryl-2a-chloro-4H-azeto[2,1-b][1,3]benzothiazin-1- ones with sodium methoxide in methanol provided indolo-1,4-benzothiazepines via a novel rearrangement. Through the sulfur extrusion reaction of indolo[2,3-b][1,4]benzothiazepines, further alkaloid-type indole derivatives, indolo[3,2-c]isoquinolines, were obtained. The structures of the new ring systems were determined by means of NMR spectroscopy.

Original languageEnglish
Pages (from-to)851-856
Number of pages6
JournalTetrahedron
Volume68
Issue number3
DOIs
Publication statusPublished - Jan 21 2012

Keywords

  • 1,3-Benzothiazine
  • IR, H and C NMR
  • Indole synthesis
  • Indolo-1,4-benzothiazepine
  • Indolo[3,2-c]isoquinoline
  • Ring transformation
  • β-Lactam

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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