Synthesis of thiazino[6,5-b]indole derivatives, analogues of the phytoalexin cyclobrassinin. A new method for preparation of 3-aminomethylindole

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Abstract

An efficient non-reductive synthesis of 3-aminomethylindole (6) was developed from gramine (1) via 3-phthalimidomethylindole (2). The reactions of amine 6 with substituted methyl dithiobenzoates gave 3- (arylthiocarbonylaminomethyl)indoles. The Hugerschoff ring-closure reactions of the thiobenzamide intermediates (11a-f) with phenyltrimethylammonium tribromide and subsequent basic treatment furnished 2-arylthiazino[6,5-b]indole derivatives (14a-f). By use of the latter bromine source, the phytoalexin cyclobrassinin (8) was prepared in a considerably higher yield than described previously. The structures of the novel products were elucidated by IR, 1H and 13C NMR spectroscopy, including 2D-HMQC, 2D-HMBC and DEPT measurements.

Original languageEnglish
Pages (from-to)9257-9262
Number of pages6
JournalTetrahedron
Volume61
Issue number39
DOIs
Publication statusPublished - Sep 26 2005

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Keywords

  • 3-Aminomethylindole
  • Hugerschoff reaction
  • Phytoalexins
  • Thiazino[6,5-b]indole

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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