127667-03-2

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 4817, 1990 DOI: 10.1021/jo00303a011

InChI:InChI=1/C15H10N2/c16-10-13-8-4-5-9-14(13)15(11-17)12-6-2-1-3-7-12/h1-9,15H/t15-/m0/s1

Upstream product

• 873-32-5 2-Chlorobenzonitrile 
• 140-29-4 phenylacetonitrile 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 109-77-3 malononitrile 
• 394-47-8 2-fluorobenzonitrile 

Downstream Products

• 1224231-10-0 1-butyl-4-phenyl-isoquinolin-3-ylamine 
• 30081-56-2 1,3,4-triphenylisoquinoline 
• 338420-83-0 1-bromo-4-phenylisoquinolin-3-amine 
• 339116-12-0 3-Oxo-1-phenyl-indan-1-carboxylic acid 
• 16618-72-7 3-phenyl-1-indanone 
• 116617-18-6 1-amino-2-(methoxycarbonyl)-3-cyano-3-phenyl-1H-indene 

Relevant academic research and scientific papers

Nickel-Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2-MeTHF: Eco-Friendly Synthesis of Aminoisoquinolines and Isoquinolones

The first example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles with arylboronic acids in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines with good functional group tolerance under mild conditions. This chemistry has also been successfully applied to the synthesis of isoquinolones by the tandem reaction of methyl 2-(cyanomethyl)benzoates with arylboronic acids. The use of the bio-based and green solvent 2-MeTHF as the reaction medium makes the synthesis process environmentally benign. The synthetic utility of this chemistry is also indicated by the synthesis of biologically active molecules.

Regioselective Access to 3-Aryl-1-aminoisoquinolines via Nickel(I)-Catalyzed C-C and C-N Cascade Coupling Reactions from the Substituted 2-(Cyanomethyl)benzonitriles

A novel and regioselective Ni(I) catalyzed C-C and C-N cascade coupling reactions has been developed. The cascade furnishes atom-economic access to 40 3-aryl-1-aminoisoquinolines. The regioselectivity of C(sp3)-cyano group over C(sp2

Aminoisoquinolines as colorimetric Hg2+ sensors: the importance of molecular structure and sacrificial base

Here it is shown that 3-phenyl-2-amino isoquinoline acts as a simple mercury sensor. It is simple to synthesize. The molecule requires base/buffer to bind in a 1:1 stoichiometry with mercury ion, however. Otherwise, it acts as a sacrificial base, presumab

Straightforward construction of diarylmethane skeletons via aryne insertion into carbon-carbon σ-bonds

Two molar amounts of arynes were found to couple with nitriles via carbon-carbon σ-bond cleavage, assembling diverse diarylmethane skeletons in a straightforward manner. The Royal Society of Chemistry.

Displacement of Halogen of 2-Halogeno-Substituted Benzonitriles with Carbanions. Preparation of (2-Cyanoaryl)arylacetonitriles

(2-Cyanoaryl)arylacetonitriles are obtained by displacement of halogen of 2-halobenzonitriles with phenylacetonitrile anions.The method also applies to a number of heteroaromatics with ortho-situated halogen and cyano groups and to heteroarylacetonitrile anions.The anions were generated by using potassium tert-butoxide or potassium carbonate.Calculated electron densities of the electrophilic centers reflect the reactivity in the displacement reaction.The calculations indicate that the potassium ion complexes with the cyano group of the 2-halobenzonitriles in nonpolar solvents, thus promoting competitive addition of the anion to the cyano group.Carbanions derived from acids with pKa ca. 19-23 similarly displaced the halogen of 2-halobenzonitriles.