Abstract
Language | English |
---|---|
Pages | 3290-3293 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 50 |
Issue number | 26 |
DOIs | |
Publication status | Published - 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
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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 journal › Article
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
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
T2 - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 26
ER -