34846-64-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Cyanoquinoline is used as a template for the development of EGFR inhibitors. These inhibitors are crucial in the treatment of various types of cancer, as they target the epidermal growth factor receptor (EGFR), which is often overexpressed in cancer cells, leading to uncontrolled cell growth and proliferation.
The use of 3-Cyanoquinoline as a template allows for the design and synthesis of novel EGFR inhibitors with improved potency, selectivity, and pharmacokinetic properties. These inhibitors can potentially be used in the treatment of non-small cell lung cancer (NSCLC), head and neck cancer, and other malignancies that rely on EGFR signaling for growth and survival.

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

Upstream product

• 69875-54-3 2,4-Dichloroquinoline-3-carbonitrile 
• 5332-24-1 3-bromoquinoline 
• 544-92-3 copper(I) cyanide 
• 151-50-8 potassium cyanide 
• 79476-07-6 3-Iodoquinoline 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 143-33-9 sodium cyanide 
• 591250-21-4 2-[acetyloxymethyl(2-nitrophenyl)]acrylonitrile 
• 557-21-1 dicyanozinc 
• 552-89-6 2-nitro-benzaldehyde 
• 225237-20-7 2-(hydroxy(2-nitrophenyl)methyl)acrylonitrile 
• 557-21-1 zinc(II) cyanide 
• 612-58-8 3-methylquinoline 

Downstream Products

• 13669-42-6 3-quinolylcarboxaldehyde 
• 6480-68-8 quinoline-3-carboxylic acid 
• 70083-49-7 N-benzyl-3-cyanoquinolinium bromide 
• 87861-96-9 3-Cyano-1-(4-trifluoromethyl-benzyl)-quinolinium; bromide 
• 6480-67-7 quinoline-3-carboxamide 
• 63124-13-0 quinoline-3-carbonitrile N-oxide 
• 350249-64-8 2-[(S)-2-benzyl-1-hydroxyethyl]-1-oxo-1,2,3,4-tetrahydrobenzo[1,3-b]naphthyridine 
• 350249-63-7 2-[2-((S)-1-Hydroxymethyl-2-phenyl-ethylamino)-ethyl]-quinoline-3-carbonitrile 

Relevant academic research and scientific papers

Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.

3-nitrile quinoline derivative and preparation method thereof

The invention discloses a 3-nitrile quinoline derivative. The structural formula of the 3-nitrile quinoline derivative is shown as a formula I, wherein R1 is hydrogen, alkyl or aryl; R2-R5 are respectively and independently hydrogen, halogen, alkyl, alkoxy, trifluoromethyl, ester group, hydroxyl or amino; and R6 is hydrogen, alkyl, ester group, aryl or substituted aryl. According to the 3-nitrile quinoline derivative provided by the invention, R1-R6 sites can be connected with various substituent groups, and the 3-nitrile quinoline derivative is an organic synthesis intermediate with wide application and has important application value in the fields of medicines and organic synthesis. The invention further provides the preparation method of the 3-nitrile quinoline derivative, the preparation method can be carried out under the air condition, the reaction condition is mild and easy to control, the used raw materials are easy to obtain, toxic nitrile compounds are not needed to serve as nitrile groups sources, the substrate application range is wide, the reaction conversion rate is high, high selectivity and yield can be obtained within short time, and the method is simple in post-treatment, green, environment-friendly and suitable for large-scale industrial production.

Nickel-Catalyzed Cyanation of Aryl Thioethers

A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Revisiting the synthesis of aryl nitriles: a pivotal role of CAN

Facilitated by the dual role of Ceric Ammonium Nitrate (CAN), herein we report a cost-effective approach for the cyanation of aryl iodides/bromides with CAN-DMF as an addition to the existing pool of combined cyanation sources. In addition to being an oxidant, CAN acts as a source of nitrogen in our protocol. The reaction is catalyzed by a readily available Cu(ii) salt and the ability of CAN to generate ammonia in the reaction medium is utilized to eliminate the additional requirement of a nitrogen source, ligand, additive or toxic reagents. The mechanistic study suggests an evolution of CN?leading to the synthesis of a variety of aryl nitriles in moderate to good yields. The proposed mechanism is supported by a series of control reactions and labeling experiments.

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

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic N-Oxides

A scalable and operationally simple method is described that allows for the chemoselective deoxygenation of a wide range of N-heterocyclic N-oxides (a total of 36 examples). This visible-light-induced protocol features the use of only commercially available reagents, room-temperature conditions, and unprecedented chemoselective removal of the oxygen atom in a quinoline N-oxide in the presence of a pyridine N-oxide in the same molecule through the judicious selection of a photocatalyst.

Cyanation of aromatic/vinylic boronic acids with α-cyanoacetates

A friendly protocol is reported to achieve cyanation of aromatic and vinylic boronic acids using nontoxic and readily available α-cyanoacetates as a cyano source under aerobic conditions. Many aryl/vinyl boronic acids (as well as some iodides and bromides) are amenable substrates to give aryl nitriles and acrylonitriles. This cyanation method provides a safe and operationally convenient alternative to traditional ones requiring toxic cyanide salts.