73013-67-9

Upstream product

• 64-17-5 ethanol 
• 1823-99-0 3-amino-3-phenylacrylonitrile 
• 529-23-7 o-aminobenzaldehyde 
• 115975-86-5 3-(2-hydroxymethylanilino)-3-phenylprop-2-enenitrile 
• 1006-67-3 5-phenylisoxazole 
• 271-58-9 anthranil 
• 614-16-4 Benzoylacetonitrile 
• 91-22-5 quinoline 
• 935-02-4 3-Phenyl-2-propynonitrile 
• 27652-35-3 (E)-2-styrylaniline 
• 1621416-90-7 (Z)-3-phenyl-3-{2-[(E)-(2-phenylethenyl)]phenylamino}acrylonitrile 
• 552-89-6 2-nitro-benzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 103457-33-6 o-nitrobenzylidene du benzoylacetonitrile 

Downstream Products

• 133348-05-7 2-phenylquinoline-3-carboxylic acid 

Relevant academic research and scientific papers

Cyanoacetylenes as Triggers and Partners in KOH-Assisted Assemblies of Quinoline-Based Dihydropyrimido[1,2- a]quinolin-3-ones on Water

Arylcyanoacetylenes trigger the assembly of dihydropyrimido[1,2-a]quinolin-3-ones in good to excellent yields on the platform of quinolines in the presence of KOH in aqueous media at room temperature. This green on-water methodology provides a simple one-pot access to a novel family of the pharmaceutically prospective compounds.

Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources

A Ru(Ⅲ)-catalyzed annulation reaction of 2-aminoaromatic aldehydes (ketones) and isoxazoles to afford diverse 3-cyanoquinolines has been developed. Notably, isoxazole acted as a cyclization reagent and nontoxic cyano source via N-O bond cleavage and fragm

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.

Copper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives

A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones or aldehydes as starting materials is reported herein. Dioxygen as the sole oxidant and hexafluoroisopropanol as the solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N-O bond cleavage and C-N/C-C bond formation features high yields and broad substrate scope.

Transition metal-free one-pot double C-H functionalization of quinolines with disubstituted electron-deficient acetylenes

Transition metal-free one-pot reaction of quinolines with acylarylacetylenes and water proceeds in the presence of KOH (55-60 °C, MeCN, 48 h) to afford 2-aryl-3-acylquinolines in up to 66% yield. Here, a formal replacement of the acetylene moiety by the aryl and acyl substituents in the quinoline scaffold takes place. In fact, it has been proved experimentally that the reaction involves the ring cleavage, accompanied by the rearrangement and insertion of the electron-deficient acetylene moiety to form a dihydroquinoline intermediate with an aldehyde functional group in position 4. This intermediate gives the corresponding doubly functionalized quinolines.

Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization

A novel regioselective synthesis of 2-aminoquinolines and 2-arylquinoline-3-carbonitriles is described via copper-mediated tandem reaction. Formation of substituted quinolines involves Knoevenagel condensation of ortho-bromobenzaldehyde with active methylene nitriles followed by copper-catalyzed reductive amination and intramolecular cyclization.

Copper-Catalyzed Aerobic Oxidative Carbocyclization Reactions of N -[(E)-Stilben-2-yl]amine Derivatives

A synthetic method for highly functionalized 2-quinolinones and quinolines has been developed. The copper(II)-catalyzed aerobic oxidative carbocyclization reactions of α-substituted N-[(E)-stilben-2-yl]acetamides, via the intramolecular carbocupration onto the alkenyl moiety, produced 3-substituted 2-quinolinones. Several useful functional groups including benzoyl, acetyl, cyano, and ethoxycarbonyl groups are compatible with the reaction conditions. This strategy was further applied to N-[(E)-stilben-2-yl]enamines to prepare 2,3-disubstituted quinolines in good yields.

Manganese(III) acetate mediated oxidative radical cyclizations of N -(2-alkenylaryl)-substituted enamines

A method has been developed for the synthesis of highly functionalized quinolines from readily available N-(2-alkenylaryl)-substituted enamines via a 6-exo-trig radical cyclization of an imine radical. Several useful functional groups including morpholinocarbonyl, benzoyl, and cyano, are compatible with the reaction conditions. Under the Mn(II)/Co(II)/O2 redox system, these N-(2-alkenylaryl)enamines were also converted into the corresponding quinolines effectively. This strategy was further applied to related 1,4-naphthoquinone derivatives, and benzo[b]acridine-6,11-diones were formed in good yields.

Cyanoacetamides (IV): Versatile one-pot route to 2-quinoline-3-carboxamides

Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlaender reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives.

Synthesis of quinolines via friedlaender reaction in water and under catalyst-free conditions

A straightforward and efficient method for the synthesis of quinolines via Friedlaender reaction of 2-aminobenzaldehyde with various ketones or malononitrile in water without using any catalyst at 70 °C is reported. Georg Thieme Verlag Stuttgart New York.