An expeditious synthesis for γ-carboline analogue 4-aryl-1,3-thiazino[6,5-b]indole derivatives via the trifluoromethanesulfonic acid-promoted isomerization of 3-amidomethylthioindole intermediates to 2-indolyl sulfides

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Abstract

A highly efficient trifluoromethanesulfonic acid-mediated rearrangement of the benzoylaminomethylthio group of 3-benzoylaminomethylthioindoles (7a-e) to position 2 of the indole ring was developed. Thus, 2-benzoylaminomethylthioindoles (9a-e) were obtained in good yields and were involved as key intermediates in the synthesis of the new γ-carboline analogue ring system: 2,9-dihydro-4-aryl-1,3-thiazino[6,5-b]indole derivatives (11a-e). The target thiazinoindoles (11a-e) were prepared via 2-thiobenzoylaminomethylindoles (10a-e) in modified Bischler-Napieralski reactions.

Original languageEnglish
Pages (from-to)1475-1480
Number of pages6
JournalTetrahedron
Volume65
Issue number7
DOIs
Publication statusPublished - Feb 14 2009

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Keywords

  • Bischler-Napieralski reaction
  • H and C NMR
  • IR
  • Isomerization
  • Thiazino[6,5-b]indole
  • Trifluoromethanesulfonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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