42108-38-3Relevant academic research and scientific papers
Synthesis of indoles via alkylidenation of acyl hydrazides
Hisler, Kevin,Commeureuc, Aurélien G.J.,Zhou, Sheng-ze,Murphy, John A.
supporting information; experimental part, p. 3290 - 3293 (2009/08/17)
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.
METHYLATION OF N-PHENYL-N'-ACETYLHYDRAZINE WITH DIMETHYL SULFATE
Barinova, V. N.,Voronin, V. G.,Zhestkov, V. P.,Portnov, Yu. N.
, p. 1609 - 1611 (2007/10/02)
The reaction of N-phenyl-N'-acetylhydrazine with dimethyl sulfate in benzene in the presence of a 40percent solution of sodium hydroxide leads to a mixture of N-methyl-N-phenyl-N'-acetylhydrazine (45percent), N,N'-dimethyl-N-phenyl-N'-acetylhydrazine (31percent), and N'-methyl-N-phenyl-N'acetylhydrazine (24percent).The dimethyl derivative is formed through the methylation of N-methyl-N-phenyl-N'-acetylhydrazine by dimethyl sulfate, whereas the other isomer does not react under these conditions.
