Synthesis of indoles via alkylidenation of acyl hydrazides

K. Hisler, A.G.J. Commeureuc, S.Z. Zhou, J.A. Murphy, EPSRC (Funder), WestCHEM (Funder)

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Abstract

Indoles have been synthesised via alkylidenation of acyl phenylhydrazides using phosphoranes and the Petasis reagent, followed by in situ thermal rearrangement of the product enehydrazines. The Petasis reagent provides an essentially neutral equivalent of the [acid-catalysed] Fischer indole synthesis, but with acyl phenylhydrazides as starting substrates. Alkylidene triphenylphosphoranes convert aroyl phenylhydrazides to indoles, but acyl phenylhydrazides derived from aliphatic carboxylic acids undergo a Brunner reaction to form indolin-2-ones.
Original languageEnglish
Pages (from-to)3290-3293
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 1 Jul 2009

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Keywords

  • stereoselective total synthesis
  • nonclassicall wittig reaction
  • carbonyl-compounds
  • substituted indoles
  • weinreb amides
  • annulation
  • heterocycles
  • conversion
  • catalyst

Cite this

Hisler, K., Commeureuc, A. G. J., Zhou, S. Z., Murphy, J. A., EPSRC (Funder), & WestCHEM (Funder) (2009). Synthesis of indoles via alkylidenation of acyl hydrazides. Tetrahedron Letters, 50(26), 3290-3293. https://doi.org/10.1016/j.tetlet.2009.02.060