882168-60-7Relevant academic research and scientific papers
Preparation of Indolenines via Nucleophilic Aromatic Substitution
Huber, Florian,Roesslein, Joel,Gademann, Karl
supporting information, p. 2560 - 2564 (2019/03/19)
An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution.
One-pot-one-step, microwave-assisted Fischer indole synthesis
Creencia, Evelyn Cuevas,Tsukamoto, Masayuki,Horaguchi, Takaaki
experimental part, p. 1095 - 1102 (2011/11/04)
The Fischer indole synthesis was carried out using microwaves instead of conventional heating procedures. When the mixture of phenylhydrazine, cyclohexanone and zinc chloride was irradiated at 600 W for 3 min, 76% of 1,2,3,4-tetrahydrocarbazole was obtained. However, when zinc chloride was replaced with p-toluenesulfonic acid (p-TSA), the reaction yielded 91% of 1,2,3,4-tetrahydrocarbazole. Thus, a series of indoles were prepared using microwaves in the presence of p-TSA catalyst.
