Synthesis of indoles via alkylidenation of acyl hydrazides

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

doi:10.1016/j.tetlet.2009.02.060

Synthesis of indoles via alkylidenation of acyl hydrazides

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

Pure And Applied Chemistry

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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 language	English
Pages (from-to)	3290-3293
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.060
Publication status	Published - 1 Jul 2009

Keywords

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

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10.1016/j.tetlet.2009.02.060

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Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)
Murphy, J., Coombs, G., Ferguson, A. & Florence, A.
Scottish Funding Council SFC, EPSRC (Engineering and Physical Sciences Research Council)
1/09/07 → 30/10/12
Project: Research

Cite this

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title = "Synthesis of indoles via alkylidenation of acyl hydrazides",

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.",

keywords = "stereoselective total synthesis, nonclassicall wittig reaction, carbonyl-compounds, substituted indoles, weinreb amides, annulation, heterocycles, conversion, catalyst",

author = "K. Hisler and A.G.J. Commeureuc and S.Z. Zhou and J.A. Murphy and {EPSRC (Funder)} and {WestCHEM (Funder)}",

year = "2009",

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doi = "10.1016/j.tetlet.2009.02.060",

language = "English",

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journal = "Tetrahedron Letters",

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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

U2 - 10.1016/j.tetlet.2009.02.060

DO - 10.1016/j.tetlet.2009.02.060

M3 - Article

VL - 50

SP - 3290

EP - 3293

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 26

ER -

Synthesis of indoles via alkylidenation of acyl hydrazides

Abstract

Keywords

Access to Document

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Cite this