1198-30-7

Usage

Uses

Used in Chemical Synthesis:
1-Isoquinolinecarbonitrile is used as a starting reagent for the syntheses of imidazo[5,1-a]isoquinolines. Its unique structure and reactivity make it a valuable component in the creation of various complex organic molecules.
Used in Material Science:
In the field of material science, 1-Isoquinolinecarbonitrile is utilized in the development of plasma-polymerized 1-isoquinolinecarbonitrile (PPIQCN). This material has potential applications in various industries due to its unique properties, which can be tailored through the plasma polymerization process.
Used in Pharmaceutical Research:
Although not explicitly mentioned in the provided materials, 1-Isoquinolinecarbonitrile's structural similarity to other bioactive compounds suggests that it may have potential applications in the pharmaceutical industry, possibly as a precursor for the development of new drugs or as a chemical probe in biological research.

Preparation

Phosphoryl chloride (0.54 g, 3.5 mmol) in chloroform (5 mL) was added dropwise to a solution of the requisite carbaldoxime (0.2 g, 1.2 mmol) in chloroform (10 mL) under ice-cooling. The mixture was heated under reflux for 4 h, treated with iced water, and the resulting precipitate was filtered off. The filtrate was basified with 28% ammonia and then extracted with chloroform to give 1-cyanoisoquinoline 1440; yield 0.17 g (95%).

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 4056, 1984 DOI: 10.1021/jo00195a036Tetrahedron Letters, 19, p. 589, 1978

InChI:InChI=1/C10H6N2/c11-7-10-9-4-2-1-3-8(9)5-6-12-10/h1-6H

Upstream product

• 1532-72-5 isoquinoline N-oxide 
• 126921-66-2 isoquinoline-1-carbaldehyde-oxime 
• 844-25-7 2-benzoyl-1-cyano-1,2-dihydroisoquinoline 
• 7677-24-9 trimethylsilyl cyanide 
• 2942-58-7 diethyl cyanophosphonate 
• 53600-01-4 2-crotonyl-1-cyano-1,2-dihydroisoquinoline 
• 103360-21-0 1-cyano-2-ethoxycarbonyl-1,2-dihydroisoquinoline 
• 1035-19-4 2-phenylsulphonyl-1,2-dihydroisoquinoline-1-carbonitrile 
• 3340-68-9 2-(toluene-4-sulfonyl)-1,2-dihydro-isoquinoline-1-carbonitrile 
• 1436-44-8 isoquinoline-1-carboxamide 
• 10026-13-8 phosphorus pentachloride 
• 145103-20-4 2-Benzoyl-1-(2-carbethoxy-3-methoxybenzyl)-1-cyan-1,2-dihydroisochinolin 
• 119-65-3 isoquinoline 
• 1721-93-3 1-methylisoquinoline 

Downstream Products

• 58022-21-2 1-acetylisoquinoline 
• 16576-23-1 1-benzoylisoquinoline 
• 486-73-7 1-isoquinolinecarboxylic acid 
• 1436-44-8 isoquinoline-1-carboxamide 
• 120332-66-3 NRB-04079 
• 120332-71-0 2-amino-1-cyanoisoquinolinium tosylate 
• 78905-67-6 1-(cyclohexyl-2-en-1-yl)isoquinoline 
• 59175-48-3 1-(1H-tetrazol-5-yl)isoquinoline 
• 58021-72-0 (isoquinolin-1-yl)(4-methoxyphenyl)methanone 
• 1402851-52-8 (S)-4-(tert-butyl)-2-(isoquinolin-1-yl)-4,5-dihydrooxazole 
• 280755-83-1 (S)-4-isopropyl-2-(isoquinolin-1-yl)-4,5-dihydrooxazole 
• 10175-00-5 1-(α-Hydroxybenzyl)isoquinoline 
• 1532-84-9 isoquinolin-1-ylamine 
• 1177408-18-2 (isoquinolin-1-yl)(4-fluorophenyl)methanone 

Relevant academic research and scientific papers

A PASE-based approach towards 12-(1H-1,2,3-triazol-1-yl)-indolo[2,1-a]isoquinolines via the reaction of 3-(isoquinolin-1-yl)-1,2,4-triazines with benzyne

12-(1H-1,2,3-Triazol-1-yl)indolo[2,1-a]isoquinolines are prepared in 51–56% yields using a PASE (pot, atom, step, economic)-based approach, namely, by the reaction between available 5-R-6-Ar-3-(isoquinolin-1-yl)-1,2,4-triazines and in situ generated benzyne. A mechanism comprising domino-transformation was suggested, and the structure of one key product was confirmed by a single crystal X-ray diffraction analysis.

Stereochemistry of c-4-bromo-r-1-cyano-t-3-methoxy-1,2,3,4- tetrahydroisoquinolines from isoquinoline Reissert compounds

Treatment of 2-acyl (or sulfonyl)-1-cyano-1,2-dihydroisoquinolines with bromine and CH3OH gave 2-acyl (or sulfonyl)-4-bromo-1-cyano-3-methoxy- 1,2,3,4-tetrahydroisoquinolines in a highly stereoselective manner in high yields. The stereochemistry, with 1,4-cis and 3,4-trans configurations, was determined by X-ray crystallography.

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

A convenient reagent for the conversion of aldoximes into nitriles and isonitriles

For the dehydroxylation of aldoximes with 4-nitro-1-((trifluoromethyl)sulfonyl)-imidazole (NTSI), slight modifications of reaction conditions resulted in significantly different reaction paths to provide either nitriles or isonitriles. The challenging conversion of aldoximes into isonitriles was achieved under mild conditions.

Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis

Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.

Synthesis method of 2-cyanoquinoline derivative

The invention discloses a synthesis method of a 2-cyanoquinoline derivative, and belongs to the technical field of synthesis methods of chinoline and derivatives thereof. The synthesis method includes: adopting a compound represented as in formula (I) and trimethylsilyl cyanide as raw materials, dissolving the raw materials in an organic solvent, catalyzing with H-diethyl phosphite and carbon tetrachloride, and adopting alkali as a deacid reagent to prepare a compound represented as in formula (II). The synthesis method of the 2-cyanoquinoline derivative has the advantages that the adopted catalysts are low in cost and easy to obtain, the raw materials are easy to store, reaction conditions are mild, experimental operations are simple, the obtained 2-cyanoquinoline derivative products are easy to purify, high yield and applicability to industrial production are realized, and a novel synthesis method for preparing the 2-cyanoquinoline derivative is provided.

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).

Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide

A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).

Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound

The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.

C?H Cyanation of 6-Ring N-Containing Heteroaromatics

Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.