Synthesis of 4-thiaharmalan analogue 4-aryl-1,3-thiazino[5,6-b]indole derivatives by prevention of rearrangements to position two of the indole moiety

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Abstract

An efficient and selective non-acidic protocol has been developed for the synthesis of derivatives of a new ring system: 4-aryl-1,3-thiazino[5,6-b]indole, a 4-thiaharmalan analogue. The convenient amidomethylation of indole-3-thiol (5) afforded 3-benzoylaminomethylthio-1H-indole (7a), with ortho-amidomethylated 2-benzoylamino-methyl-3-benzoylaminomethylthio-1H-indole (8) as side product. Following the Bischler-Napieralski reaction of 7a the rearranged 2-benzoylaminomethylthio-1H-indole 11 could be isolated. In order to prevent such rearrangements the target thiazinoindoles were prepared via 3-thiobenzoylaminomethylthioindole (13) via a modified Bischler-Napieralski reaction.

Original languageEnglish
Pages (from-to)8646-8651
Number of pages6
JournalTetrahedron
Volume64
Issue number37
DOIs
Publication statusPublished - Sep 8 2008

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Keywords

  • 4-Thiaharmalan
  • Amidomethylation
  • Bischler-Napieralski reaction
  • Thiazino[5,6-b]indole

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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