88115-31-5

Usage

Structure

An indole ring attached to an acetonitrile group and a sulfonyl group

Usage

Commonly used in organic synthesis as a building block for the preparation of various pharmaceuticals and agrochemicals

Potential

Studied for its potential as a precursor to new drugs and as an intermediate in the synthesis of biologically active compounds

Biological activities

Exhibits various biological activities, including anticancer and antiparasitic properties, making it a valuable compound in medicinal chemistry research.

Upstream product

• 771-51-7 indole-3-acetonitrile 
• 98-59-9 p-toluenesulfonyl chloride 
• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 

Downstream Products

• 1068458-86-5 1-[(1-p-toluenesulfonyl-1H-indol-3-yl)methyl]cyclopropylamine 

Relevant academic research and scientific papers

Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions

We introduce readily available ammonium hemiaminals as O-transfer reagents and commercially available acetonitriles as a primary amide enolate precursor. The combination serves as an amide enolate equivalent, thereby providing one-pot access to α-substituted indolylacetamides. A broad substrate scope and good functional group tolerance as well as gram-scale synthesis make this protocol highly attractive. Mechanistic experiments suggest that the cyano group is trapped by a hydroxy group of hemiaminals en route to the desired primary amides under metal-free conditions.

Preparation method of aryl acetonitrile derivative

The invention relates to a continuous nucleophilic addition and beta-fluorine elimination reaction method of 2,2-difluoroolefin and ammonia water in a catalyst-free and additive-free system. The method comprises the following steps: adding a 2,2-difluoroolefin compound, ammonia water and a solvent into a Schlenk reaction flask, and conducting stirring and reacting at a certain temperature in an air atmosphere to obtain the product aryl acetonitrile derivative.

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.

Synthesis of new cyclopropanated tryptamine analogues

A series of tryptamine analogues bearing a cyclopropyl-amine unit was prepared, starting from 3-indolyl acetonitriles, through a MeTi(Oi-Pr) 3-mediated cyclopropanation. Georg Thieme Verlag Stuttgart.