64359-09-7

Upstream product

• 1075-76-9 N-cyanoethylaniline 
• 673-32-5 1-Phenylprop-1-yne 
• 55919-60-3 N-(2-cyanoethyl)-N-phenylnitrosamine 
• 10257-92-8 2-phenyl-3-methyl-1H-indole 
• 107-13-1 acrylonitrile 

Relevant academic research and scientific papers

Rhodium(III)-catalyzed indole synthesis using N-N bond as an internal oxidant

We report herein a Rh(III)-catalyzed cyclization of N-nitrosoanilines with alkynes for streamlined synthesis of indoles. The synthetic protocol features a distinct internal oxidant, N-N bond, as a reactive handle for catalyst turnover, as well as a hitherto tantalizingly elusive intermolecular redox-neutral manifold, predicated upon C-H activation, for the formation of a five-membered azaheterocycle. The compatibility of seemingly dichotomous acidic and basic conditions ensures reaction versatility for multifarious synthetic contexts. The tolerance of an array of auxiliary functional groups potentially permits predefined, programmable substitution patterns to be incorporated into the indole scaffold. Comprehensive mechanistic studies, under acidic condition, support [RhCp*]2+ as generally the catalyst resting state (switchable to [RhCp*(OOCtBu)]+ under certain circumstance) and C-H activation as the turnover-limiting step. Given the variety of covalent linkages available for the nitroso group, this labile functionality is likely to be harnessed as a generic handle for strikingly diverse coupling reactions.

Acylation, cyanoethylation and alkylation of methyl and phenyl indolylmagnesium salts: Influence of the substituents on the C- and N- reaction products

Analysis of the influence of the substitution on indolylmagnesium salts in the reaction with benzoyl chloride, acrylonitrile and methyl iodide, giving the C- and N-derivatives, have been carried out. The yield in the C- and N-product depends upon the electronic character and position of the substituent (methyl or phenyl) on the indole ring and of the ethereal solvent as well as the concentration and molar ratio of the reagents. The 2- or 3- phenyl substituted indolylmagnesium salts with acrylonitrile always gave the 1-(2-cyanoethyl)indole derivative.

2-Substituted-indole-1-lower-alkanecarboxamides

2-Substituted-indole-1-lower-alkanecarboxamides, prepared by amidation of the corresponding acid or ester; by hydrolysis or thiohydrolysis of the corresponding carbonitrile; by alkylation of a suitable indole with a halo-lower-alkanecarboxamide; or by hydrolysis of a 1-indolechlorosulfonylcarbamyl derivative, have anti-secretory and anti-ulcer activities.