Tetrahedron Letters

Synthesis of indoles via alkylidenation of acyl hydrazides

K Hisler, AGJ Commeureuc, S Zhou, JA Murphy

Index: Hisler, Kevin; Commeureuc, Aurelien G.J.; Zhou, Sheng-ze; Murphy, John A. Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3290 - 3293

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Citation Number: 20

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, ...