76061-97-7

Upstream product

• 4173-66-4 3-[(4-methylphenyl)amino]-1-phenyl-1-propanone 
• 1198272-70-6 4-methyl-N-(prop-2-yn-1-yl)-N-(p-tolyl)benzenesulfonamide 
• 1220993-62-3 4-methyl-N-(3-phenylprop-2-yn-1-yl)-N-(p-tolyl)benzenesulfonamide 
• 599-86-0 4-methyl-N-(4-methylphenyl)benzenesulfonamide 
• 106-49-0 p-toluidine 
• 104-55-2 3-phenyl-propenal 
• 2579-22-8 Phenylpropargyl aldehyde 
• 60-12-8 2-phenylethanol 
• 32328-79-3 4-methyl-N-methyleneaniline 
• 91-62-3 6-methylquinoline 
• 98-80-6 phenylboronic acid 
• 49634-76-6 1-phenyl-1-(2-amino-5-methylphenyl)ethylene 
• 67-68-5 dimethyl sulfoxide 
• 536-74-3 phenylacetylene 

Downstream Products

• 76061-91-1 2-Chloro-1-(6-methyl-4-phenyl-3,4-dihydro-2H-quinolin-1-yl)-ethanone 
• 76061-84-2 N-[2-(6-Methyl-4-phenyl-3,4-dihydro-2H-quinolin-1-yl)-2-oxo-ethyl]-guanidine; hydrochloride 
• 76062-02-7 2-Amino-1-(6-methyl-4-phenyl-3,4-dihydro-2H-quinolin-1-yl)-ethanone 

Relevant academic research and scientific papers

Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines

A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination of CO2 cascade processes.

DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles

Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxide-promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N-H bond or α-C-H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.

Lewis acid catalyzed reactivity switch: Pseudo three-component annulation of nitrosoarenes and (epoxy)styrenes

A Lewis acid catalyzed annulation reaction via arene functionalization of nitrosoarenes and C-C cleavage of (epoxy)styrene to provide arylquinolines is reported. The Lewis acid catalyst altered the annulation pattern providing arylquinolines instead of oxazolidines. The reaction with styrene resulted in a mixture of 2,4-diarylquinoline and 4-Arylquinoline, while only 3-Arylquinoline was formed from the reaction of epoxystyrene. This journal is

Microwave-Assisted Metal-Free Rapid Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reaction

A rapid microwave assisted, (±) camphor-10-sulfonic acid (CSA) promoted, Povarov type multicomponent synthesis of 4-arylated quinolines from anilines, alkynes, and paraformaldehyde is described. This reaction proceeds through [4+2] cycloaddition of imine (formed in situ from aniline and paraformaldehyde) and alkynes in the presence of CSA, without any metal catalyst. Mechanistic study revealed that CSA inhibit the synthesis of Troger's base and assist the cycloaddition of imines with alkynes by activating the imine.

Method for synthesizing substituted quinoline derivative 4- through palladium catalysis (by machine translation)

The invention belongs to the technical field of 4 - synthetic chemistry, and particularly. relates to a method for synthesizing a substituted quinoline derivative with palladium through palladium catalysis, Cs. 2 CO3 The method disclosed by, the 60-80 °C invention is 5-8 simple, and green, in 4 - synthetic process,has excellent selectivity and high yield, and has a wide substrate range, and the method has a wide, application value in the fields of pharmaceutical chemistry, biochemistry and the like. (by machine translation)

CONVERSION OF TETRAHYDROQUINOLINE DERIVATIVES TO QUINOLINE USING AZOCOMPOUND

The present invention relates to a method of converting tetrahydroquinoline derivatives into quinoline using an azo compound and, more specifically, to a conversion method which is performed in a deuterium chloroform (CDCl_3) or chloroform (CHCl_3) solution including dialkyl azodicarboxylate, which is a method of producing quinoline through a dehydrogenation reaction of 1,2,3,4-tetrahydroquinoline. According to the present invention, a dehydrogenation reaction rate is dependent on the electronic and steric properties of used dialkyl azodicarboxylate; and chloroform shows better results than other substances in solvents screened with diethyl azodicarboxylate. Various types of 1,2,3,4-tetrahydroquinoline undergo the dehydration reaction of the present invention to produce the corresponding quinoline in a yield of at least 90%; and diethyl hydrazo dicarboxylate, which is a reduced form of diethyl azodicarboxylate, is readily separated and recyclable.COPYRIGHT KIPO 2020

Transition-Metal-Free Approach for the Synthesis of 4-Aryl-quinolines from Alkynes and Anilines

An efficient and transition-metal-free approach for the synthesis of 4-arylquinolines from readily available anilines and alkynes in the presence of K2S2O8 and DMSO has been developed. A variety of alkynes and anilines having a diverse range of substitution patterns can undergo the one-pot cascade process successfully. Effectively, this method uses DMSO as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 4-arylquinolines.

Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C-H Activation/Cyclization of Anilines with Alkynes

A unique Co(III)-catalyzed and DMSO-involved C-H activation/cyclization of simple, cheap, and easily available anilines with alkynes for direct and highly efficient synthesis of privileged quinolines with exclusive regioselectivity and broad substrate/functional group tolerance and in good to excellent yields, where DMSO was employed as both the solvent and the C1 building block of quinoline products, is reported. Mechanistic experiments revealed that the versatile reaction might employ the 2-vinylbenzenamine species as the active intermediate.

Synthesis of quinolines from anilines, acetophenones and DMSO under air

An efficient CH3SO3H-promoted synthesis of quinolines from readily available anilines, acetophenones and DMSO under air is reported. This protocol gives diverse substituted 4-arylquinolines in moderate to high yields with broad substrate/functional group tolerance. Preliminary mechanistic studies demonstrate that DMSO may be transformed to HCHO in this process and used as a one carbon source.

Efficient dehydrogenation of 1,2,3,4-tetrahydroquinolines mediated by dialkyl azodicarboxylates

Various dialkyl azodicarboxylates were investigated for the dehydrogenation of 1,2,3,4-tetrahydroquinolines to quinolines. The dehydrogenation rates varied according to the electronic and steric nature of the used dialkyl azodicarboxylates. Among solvents screened with diethyl azodicarboxylate, chloroform exhibited superior results to others. A variety of 1,2,3,4-tetrahydroquinolines underwent the present dehydrogenation to produce the corresponding quinolines. Diethyl hydrazodicarboxylate, which is a reduced species of diethyl azodicarboxylate, was easily separated for recycle.