Synthesis of indoles via alkylidenation of acyl hydrazides

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

Research output: Contribution to journalArticle

20 Citations (Scopus)

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.
LanguageEnglish
Pages3290-3293
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 1 Jul 2009

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Indoles
Phosphoranes
Carboxylic Acids
Fatty Acids
Hot Temperature
Acids
phenylhydrazine
Substrates

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
Hisler, K. ; Commeureuc, A.G.J. ; Zhou, S.Z. ; Murphy, J.A. ; EPSRC (Funder) ; WestCHEM (Funder). / Synthesis of indoles via alkylidenation of acyl hydrazides. In: Tetrahedron Letters. 2009 ; Vol. 50, No. 26. pp. 3290-3293.
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Hisler, K, Commeureuc, AGJ, Zhou, SZ, Murphy, JA, EPSRC (Funder) & WestCHEM (Funder) 2009, 'Synthesis of indoles via alkylidenation of acyl hydrazides' Tetrahedron Letters, vol. 50, no. 26, pp. 3290-3293. https://doi.org/10.1016/j.tetlet.2009.02.060

Synthesis of indoles via alkylidenation of acyl hydrazides. / Hisler, K.; Commeureuc, A.G.J.; Zhou, S.Z.; Murphy, J.A.; EPSRC (Funder); WestCHEM (Funder).

In: Tetrahedron Letters, Vol. 50, No. 26, 01.07.2009, p. 3290-3293.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of indoles via alkylidenation of acyl hydrazides

AU - Hisler, K.

AU - Commeureuc, A.G.J.

AU - Zhou, S.Z.

AU - Murphy, J.A.

AU - EPSRC (Funder)

AU - WestCHEM (Funder)

PY - 2009/7/1

Y1 - 2009/7/1

N2 - 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.

AB - 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.

KW - stereoselective total synthesis

KW - nonclassicall wittig reaction

KW - carbonyl-compounds

KW - substituted indoles

KW - weinreb amides

KW - annulation

KW - heterocycles

KW - conversion

KW - catalyst

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DO - 10.1016/j.tetlet.2009.02.060

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JO - Tetrahedron Letters

T2 - Tetrahedron Letters

JF - Tetrahedron Letters

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Hisler K, Commeureuc AGJ, Zhou SZ, Murphy JA, EPSRC (Funder), WestCHEM (Funder). Synthesis of indoles via alkylidenation of acyl hydrazides. Tetrahedron Letters. 2009 Jul 1;50(26):3290-3293. https://doi.org/10.1016/j.tetlet.2009.02.060