37039-47-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile is used as a starting material or intermediate in the synthesis of various bioactive molecules, such as pharmaceuticals or agrochemicals. Its unique structural features, including the benzyl and tetrahydroisoquinoline moieties, contribute to its potential for developing new drugs with therapeutic benefits.
Used in Chemical Industry:
2-Benzyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile may have industrial applications in the production of dyes or pigments, where its chemical properties and structural features can be utilized to create novel colorants for various applications.

Upstream product

• 151-50-8 potassium cyanide 
• 84500-82-3 2-benzyl-3,4-dihydroisoquinolin-2-ium bromide 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 532-28-5 (RS)-mandelonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 13605-95-3 N-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 100-46-9 benzylamine 
• 6772-61-8 2-(4-benzylphenyl)-3,4-dihydroisoquinolin-1(2H)-one 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 100-39-0 benzyl bromide 

Downstream Products

• 40615-06-3 (2-benzyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methanamine 
• 84500-83-4 2-benzyl-1-<(isopropylamino)methyl>-1,2,3,4-tetrahydroisoquinoline 
• 1346425-09-9 2-benzyl-1,2,3,4-tetrahydroisoquinoline-3-carbonitrile 
• 1225494-20-1 2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylacetonitrile 
• 79848-93-4 N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclohexanecarboxylic acid amide 
• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 

Relevant academic research and scientific papers

Electrochemically promoted oxidative α-cyanation of tertiary and secondary amines using cheap AIBN

The electrochemical α-cyanation of tertiary and secondary amines has been developed by using a cheap cyanide reagent, azobisisobutyronitrile (AIBN). The CN radical, generated throughn-Bu4NBr-meidated electrochemical oxidation, participates in a novel α-cyanation reaction under exogenous oxidant-free conditions.

Transition-Metal-Free Reductive Functionalization of Tertiary Carboxamides and Lactams for α-Branched Amine Synthesis

A new method for the synthesis of α-branched amines by reductive functionalization of tertiary carboxamides and lactams is described. The process relies on the efficient and controlled reduction of tertiary amides by a sodium hydride/sodium iodide composite, in situ treatment of the resulting anionic hemiaminal with trimethylsilyl chloride and subsequent coupling with nucleophilic reagents including Grignard reagents and tetrabutylammonium cyanide. The new method exhibits broad functional-group compatibility, operates under transition-metal-free reaction conditions, and is suitable for various synthetic applications on both sub-millimole and on multigram scales.

Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation

A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.

Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations

A one-pot, three-component synthesis of widely substituted isoindolinones and isoquinolinones, featuring a Lewis acid-catalyzed efficient Strecker reaction and lactamization sequence, affording products in good to high yields is reported. The method has also been extended to the synthesis of tetrahydroisoquinolines (THIQs) in high yields. (Chemical Equation Presented).

Mechanochemical Strecker Reaction: Access to α-Aminonitriles and Tetrahydroisoquinolines under Ball-Milling Conditions

A mechanochemical version of the Strecker reaction for the synthesis of α-aminonitriles was developed. The milling of aldehydes, amines, and potassium cyanide in the presence of SiO2gave the corresponding α-aminonitriles in good to high yields. The high efficiency of the mechanochemical Strecker-type multicomponent reaction allowed the one-pot synthesis of tetrahydroisoquinolines after a subsequent internal N-alkylation reaction.

A versatile C-H functionalization of tetrahydroisoquinolines catalyzed by iodine at aerobic conditions

A versatile aerobic catalytic system (I2 and O2/TBHP) for C-H functionalization is reported. This CDC (cross-dehydrogentive coupling) reaction is compatible with a large number of nucleophiles and is performed under ambient reaction

Redox-neutral α-cyanation of amines

α-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine α-cyanation/N-alkylation or alternatively, α-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.

Synthesis of 1-(Aminomethyl)-1,2,3,4-tetrahydroisoquinolines and Their Actions at Adrenoceptors in Vivo and in Vitro

An improved synthesis of 1-(aminomethyl)-1,2,3,4-tetrahydroisoquinolines has been developed by using aluminum hydride reduction of 1-cyano-1,2,3,4-tetrahydroisoquinolines.Three 1-(aminomethyl)-6,7-dihydroxytetrahydroisnolines