117679-34-2

Upstream product

• 3009-97-0 N-phenylglycinonitrile 
• 106-95-6 allyl bromide 
• 62-53-3 aniline 
• 67-56-1 methanol 
• 7677-24-9 trimethylsilyl cyanide 
• 6628-07-5 N-allyl-N-methylaniline 
• 589-09-3 N-allyl-N-phenylamine 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 117679-35-3 2-(N-allylanilino)-2Z,4E-hexadienenitrile 
• 117679-45-5 2-(N-allylanilino)-2E,4E-hexadienenitrile 
• 199472-23-6 2-(N-allylanilino)-3-(o-bromophenyl)propanenitrile 
• 117679-42-2 4-benzyl-2-cyano-1-phenyl-4,5-dihydro-1H-azepine 
• 117679-40-0 2-cyano-4-ethyl-1-phenyl-4,5-dihydro-1H-azepine 
• 117679-37-5 2-(N-allylanilino)-5-phenyl-2Z,4E-pentadienenitrile 
• 117679-47-7 2-(N-allylanilino)-5-phenyl-2E,4E-pentadienenitrile 

Relevant academic research and scientific papers

Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines

Iron-catalyzed oxidative α-cyanations at tertiary allylamines in the allylic position are followed by anti-Markovnikov additions of alcohols across the vinylic CC double bonds of the initially generated α-amino nitriles. These consecutive reactions generate 2-amino-4-alkoxybutanenitriles from three reactants (allylamines, trimethylsilyl cyanide, and alcohols) in one reaction vessel at ambient temperature.

Preparation method for alpha-cyanoamine

The invention discloses a preparation method for alpha-cyanoamine. According to the method, the product alpha-cyanoamine is prepared through nucleophilic substitution in a mixed solvent in the presence of an oxidizing agent with an amine compound and cyanoacetic acid as reactants, iodide as a catalyst and sodium acetate as alkali. The catalyst used in the method has high reactivity; reaction conditions are mild; the application scope of a substrate is wide; post-treatment is convenient; the yield of the target product is high; preparation process is simple, green and environment-friendly; and used raw materials are widely available.

Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids

Using cyanoacetic acid as a masked electrophile, a new cyanomethylation reaction of amines and carboxylic acids was developed, producing a variety of α-aminonitriles and cyanomethyl esters with good yields and excellent functionality tolerance. This protocol features simple manipulation, inexpensive reagents, and a wide substrate scope. Iodoacetonitrile was generated in situ from the iodination-decarboxylation of cyanoacetic acid in this transformation.

Palladium-catalyzed chemoselective intramolecular cyclization of bromoanilinoalkenenitriles

α-(o-Bromoanilino)alkenenitriIes 1a-f and 2a-e and α-(N-alkenylamino)-β-(o-bromophenyl)-propanenitriles 7a-c and 8a-c undergo palladium-catalyzed conversion into o-(methylamino)benzonitrile 12, o-[(alkenylamino)ethenyl]benzonitriles 24a-c, N-alkenylanilines 26b, 26c, 3-benzazepines 29a, 29c, 31a and 32a, γ-carbolines 36 and pyrrolo[3,2-b]indole 45. The reactions involve intramolecular additions of arylpalladium to the cyano group and subsequent processes such as cyano group transposition, hydrolysis, electrocyclization, ethyl group transfer and oxidative aromatization. A general mechanism for the palladium-catalyzed arylation of a cyano group is proposed.