35509-27-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 8224, 1998 DOI: 10.1021/jo9808674

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

Upstream product

• 143-33-9 sodium cyanide 
• 108530-08-1 quinolin-8-yl trifluoromethanesulfonate 
• 16567-18-3 8-bromoquinoline 
• 916314-51-7 quinolin-8-yl methanesulfonate 
• 148-24-3 8-quinolinol 
• 10522-42-6 toluene-4-sulfonic acid quinolin-8-yl ester 
• 38707-70-9 8-formylquinoline 
• 557-21-1 zinc(II) cyanide 
• 937640-02-3 8-bromo-1,2,3,4-tetrahydroquinoline 
• 133042-65-6 8-<(Fluorosulfonyl)oxy>naphthalene 
• 151-50-8 potassium cyanide 
• 611-33-6 8-chloroquinoline 
• 611-32-5 8-methylquinoline 

Downstream Products

• 54885-04-0 phenyl(quinolin-8-yl)methanone 
• 62216-06-2 quinoline-8-carbothioic acid amide 
• 86-59-9 8-carboxyquinoline 
• 55706-61-1 quinoline-8-carboxamide 

Relevant academic research and scientific papers

Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group

Pd-catalyzed directing-group-assisted regioselective halogenations to C7 of indolines and C8 of tetrahydroquinolines were achieved in good to excellent yields. The practicality and utility of the developed method have been illustrated by various functiona

Preparing method of aromatic nitrile or alkenyl nitrile compound

The invention discloses a preparing method of an aromatic nitrile or alkenyl nitrile compound. The preparing method comprises the following step that under protection of inert gas, an aryl or heteroaryl sulphonate compound shown in a formula II or an alkenyl sulphonate compound shown in a formula IV and a cyanation reagent are subjected to a cross-coupling reaction as is shown below in a solvent under the condition of the presence of a nickel complex, metal zinc and an additive to obtain the aromatic nitrile or alkenyl nitrile compound, wherein 4-dimethylamiopryidine (DMAP) is adopted as the additive, and zinc cyanide is adopted as the cyanation reagent. By means of the preparing method, cyanation of aryl sulphonate, heteroaryl sulphonate or alkenyl sulphonate can be simply and efficientlyachieved with a cheap catalysis system; moreover, the functional group compatibility and substrate universality are good, and a better application prospect and higher using value are provided for achieving industrial synthesis of the aromatic nitrile or alkenyl nitrile compound.

PYRAZOLO-TRIAZINE AND/OR PYRAZOLO-PYRIMIDINE DERIVATIVES AS SELECTIVE INHIBITOR OF CYCLIN DEPENDENT KINASE

The present invention relates to pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[l,5-a]pyrimidine derivatives and/or pharmaceutically acceptable salts thereof, the use of these derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of cell proliferative diseases, inflammatory diseases, immunological diseases, cardiovascular diseases and infectious diseases. Furthermore, the present invention is directed towards pharmaceutical compositions containing at least one of the pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[1,5-a]pyrimidine derivatives and/or pharmaceutically acceptable salts thereof.

Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)2 Involving C-O Bond Cleavage

An efficient nickel-catalyzed cyanation of aryl sulfonates, fluorosulfonates, and sulfamates with Zn(CN)2 was developed, which provides a facile access to the nitrile products in generally good to excellent yields. The reaction is accomplished by using NiII complex as the precatalyst and DMAP as the additive. The method also displays wide functional group compatibility; for example, keto, methoxy, N,N-dimethylamino, cyano, ester, and pyridyl groups are well-tolerated during the reaction process.

Aryl nitrile compound preparation method

The present invention provides a preparation method of an aryl nitrile compound having a general formula I, wherein the general formula I is defined in the specification. The preparation method comprises: adopting an aryl compound having a general formula II as a substrate, wherein the general formula II is defined in the specification, n is 0-1, X1, X2, X3 and X4 are independently and respectively any one selected from N, S, O and C in chemically acceptable structures, Y is OSO2F, OTf or OTs, and R1, R2, R3 and R4 are independently and respectively any one selected from H, alkyl, aryl and halogen; and carrying out a cyanation reaction on the aryl compound and a cyanogen source under the catalysis effect of a catalyst, a reducing agent and a ligand to obtain the aryl nitrile compound. With the preparation method of the present invention, the aryl nitrile compound preparation cost can be reduced, the required reaction temperature is low, the requirements on the catalyst is low, the conversion rate is high, and the preparation method is suitable for various aryl or miscellaneous aryl substrates containing electron-rich or electron-deficient substituents.

Synthesis of nitriles from aldehydes with trimethylphenylammonium tribromide and ammonium acetate

Various aromatic and heterocyclic aldehydes were easily converted to respective nitriles with the combination of trimethylphenylammonium tribromide and ammonium acetate in good yields at room temperature.

Aerobic Copper-Promoted Radical-Type Cleavage of Coordinated Cyanide Anion: Nitrogen Transfer to Aldehydes to Form Nitriles

We have disclosed for the first time the copper-promoted C≡N triple bond cleavage of coordinated cyanide anion under a dioxygen atmosphere, which enables a nitrogen transfer to various aldehydes. Mechanistic study of this unprecedented transformation suggests that the single electron-transfer process could be involved in the overall course. This protocol provides a new cleavage pattern for the cyanide ion and would eventually lead to a more useful synthetic pathway to nitriles from aldehydes.

Iodine-catalyzed ammoxidation of methyl arenes

The development of organic transformation using cheap and readily available substrates under mild conditions will be pivotal for green and sustainable synthetic organic chemistry. Concerning our continued interest in the cyanation reaction, a metal-free direct ammoxidation of readily available methyl arenes leading to nitriles was established under mild conditions. A series of aryl methanes especially heteroaryl methanes (30 examples) were applicable in moderate to good yields with good functionality tolerance.

A mild and efficient palladium-catalyzed cyanation of aryl mesylates in water or tBuOH/water

Cool and compatible: Aryl mesylates and tosylates underwent palladium-catalyzed cyanation under mild, aqueous conditions at 65-80°C (see scheme). In many cases, water could be used as the reaction medium without a cosolvent, and a variety of substituents R, such as keto, aldehyde, ester, free amine, and nitrile groups, remained intact during the transformation. Cy=cyclohexyl, Ms=methanesulfonyl, Ts=p-toluenesulfonyl.

Design, synthesis, and evaluation in vitro of quinoline-8-carboxamides, a new class of poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) inhibitor

Poly(ADP-ribose)polymerase-1 is an important target enzyme in drug design; inhibitors have a wide variety of therapeutic activities. A series of quinoline-8-carboxamides was designed to maintain the required pharmacophore conformation through an intramolecular hydrogen bond. 3-Substituted quinoline-8-carboxamides were synthesized by Pd-catalyzed couplings (Suzuki, Sonogashira, Stille) to 3-iodoquinoline-8-carboxamide, an efficient process that introduces diversity in the final step. 2-Substituted quinoline-8-carboxamides were prepared by selective Pd-catalyzed couplings at the 2-position of 2,8-dibromoquinoline, followed by lithium-bromine exchange of the intermediate 2-(alkyl/aryl)-8-bromoquinolines and reaction with trimethylsilyl isocyanate. The intramolecular hydrogen bond was confirmed by X-ray and by NMR. The SAR of the 3-substituted compounds for inhibition of human recombinant PARP-1 activity showed a requirement for a small narrow group. Substituents in the 2-position increased potency, with the most active 2-methylquinoline-8-carboxamide having IC50 = 500 nM (IC50 = 1.8 μM for 5-aminoisoquinolin-1- one (5-AIQ, a standard water-soluble inhibitor)).