5467-79-8

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 5745, 1985 DOI: 10.1021/ja00306a024

InChI:InChI=1/C11H8N2O/c1-14-10-4-5-11-8(6-10)2-3-9(7-12)13-11/h2-6H,1H3

Upstream product

• 6563-13-9 6-methoxyquinoline N-oxide 
• 151-50-8 potassium cyanide 
• 98-88-4 benzoyl chloride 
• 5263-87-6 6-methoxy quinoline 
• 98-59-9 p-toluenesulfonyl chloride 
• 91523-19-2 6-Methoxy-1-(toluene-4-sulfonyl)-1,2-dihydro-quinoline-2-carbonitrile 
• 110-86-1 pyridine 
• 13676-02-3 2-chloro-6-methoxyquinoline 
• 506-64-9 silver(I) cyanide 
• 330660-35-0 silver cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 52313-34-5 6-hydroxyquinoline-2-carbonitrile 
• 74-88-4 methyl iodide 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 75433-99-7 6-Methoxy-quinoline-2-carboxylic acid 
• 19062-88-5 2-Cyan-7-methoxy-benz-(1,3)-oxazepin 
• 119990-33-9 2-amino-6-methoxy quinoline 
• 1453101-20-6 N-(6-methoxy-2-methylquinolin-7-yl)-N-(phenylsulfonyl)benzenesulfonamide 
• 1453101-37-5 N,N'-(6-methoxy-2-methylquinoline-5,7-diyl)bis(N-(phenylsulfonyl)benzenesulfonamide) 
• 122364-83-4 (S)-2-(6-hydroxyquinolin-2-yl)-4,5-dihydrothiazole-4-carboxylic acid 
• 1289513-16-1 tert-butyl 1-(3-(2-cyanoquinolin-6-yloxy)propylamino)-1-oxo-3-(tritylthio)propan-2-ylcarbamate 

Relevant academic research and scientific papers

Selective naphthalene H3 receptor inverse agonists with reduced potential to induce phospholipidosis and their quinoline analogs

We reported earlier the refinement of our initial five-point pharmacophore model for the Histamine 3 receptor (H3R), with a new acceptor feature important for binding and selectivity against the other histamine receptor subtypes 1, 2 and 4. This approach was validated with a new series of H3R inverse agonists: the naphthalene series. In this Letter, we describe our efforts to overcome the phospholipidosis flag identified with our initial lead compound (1a). During the optimization process, we monitored the potency of our molecules toward the H3 receptor, their selectivity against H1R, H2R and H4R, as well as some key molecular properties that may influence phospholipidosis. Encouraged by the promising profile of the naphthalene series, we used our deeper understanding of the H3R pharmacophore model to lead us towards the quinoline series. This series is perceived to have intrinsic advantages with respect to its amphiphilic vector.

Highly Potent and Selective MT2 Melatonin Receptor Full Agonists from Conformational Analysis of 1-Benzyl-2-acylaminomethyl-tetrahydroquinolines

Molecular superposition models guided the design of novel melatonin receptor ligands characterized by a 2-acylaminomethyltetrahydroquinoline scaffold. Starting from the structure of N-anilinoethylamide ligands, the flexible chain was conformationally cons

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.).

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.

Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)-Catalyzed Hydrogenation of 2,2′-Bisquinoline Derivatives

An asymmetric hydrogenation of 2,2′-bisquinoline and bisquinoxaline derivatives, catalyzed by chiral cationic ruthenium diamine complexes, was developed. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereo- and enantioselectivity (up to 93:7 dl/meso and >99 % ee). These chiral diamines could be easily transformed into a new class of chiral N-heterocyclic carbenes (NHCs), which are important but difficult to access.

QUINOLINE DERIVATIVES AS H3R INVERSE AGONISTS

The present invention relates to compounds of formula I: and pharmaceutically acceptable salts thereof as well as to pharmaceutical compositions comprising these compounds and to methods for their preparation. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors.

Bicyclo 4.4.0 antiviral derivatives

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with amido piperazine derivatives. These compounds possess unique antiviral activity