Swern oxidation of tryptamine derivatives

Patrick D. Bailey, Philip J. Cochrane, Frances Irvine, Keith M. Morgan, D. P J Pearson, Kenneth T. Veal

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The Swern oxidation of various indolic substrates is described, and a range of products resulting from overall oxidation at the 2-position were observed. In particular, depending on the substrate and reaction conditions, it was possible to achieve direct oxidation to a, ß-unsaturated systems at the 2-position, to introduce a nucleophile at the 2-position, and to introduce a CH3-S-CH2 group at the indole 4-position via an unprecedented rearrangement of a Swern intermediate.

Original languageEnglish
Pages (from-to)4593-4596
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number24
DOIs
Publication statusPublished - 11 Jun 1999

Keywords

  • Indoles
  • Oxidation
  • Rearrangements
  • Swern

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