Synthesis of indoles via alkylidenation of acyl hydrazides

Indoles have been synthesised via alkylidenation of acyl hydrazides using (i) phosphoranes and (ii) the Petasis reagent. Indoles have been synthesised via alkylidenation of acyl phenylhydrazides using phosphoranes and the Petasis reagent, followed by in situ thermal rearrangement of the product eneh...

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Bibliographic Details
Published in:Tetrahedron letters 2009-07, Vol.50 (26), p.3290-3293
Main Authors: Hisler, Kevin, Commeureuc, Aurélien G.J., Zhou, Sheng-ze, Murphy, John A.
Format: Article
Language:English
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Summary:Indoles have been synthesised via alkylidenation of acyl hydrazides using (i) phosphoranes and (ii) the Petasis reagent. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.02.060