861872-54-0

Upstream product

• 936-59-4 3-chloropropiophenone 
• 106-40-1 4-bromo-aniline 
• 50-00-0 formaldehyd 
• 98-86-2 acetophenone 
• 67-68-5 dimethyl sulfoxide 
• 536-74-3 phenylacetylene 
• 98-80-6 phenylboronic acid 
• 6563-11-7 6-bromoquinoline-N-oxide 
• 1448444-04-9 6-bromo-4-phenyl-1,2,3,4-tetrahydroquinoline 
• 189252-18-4 1-phenyl-1-(2-amino-5-bromophenyl)ethylene 
• 298-12-4 Glyoxilic acid 
• 5332-25-2 6-bromoquinoline 
• 107047-10-9 p-bromobenzylazide 

Downstream Products

• 861872-55-1 C₁₅H₁₀BrNO 

Relevant academic research and scientific papers

The one-pot synthesis of quinolines: Via Co(iii)-catalyzed C-H activation/carbonylation/cyclization of anilines

We herein disclose a novel Co(iii)-catalyzed C-H activation/carbonylation/cyclization of anilines with ketones using paraformaldehyde as the carbonyl source, giving direct access to diverse quinolines with broad functional group tolerance and in good to excellent yields. Moreover, exclusive site-/region-selectivity was observed in this versatile transformation.

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.

Direct arylation for the synthesis of 2-arylquinolines from N-methoxyquinoline-1-ium tetrafluoroborate salts and arylboronic acids

A rapid and direct arylation reaction of N-methoxyquinoline-1-ium tetrafluoroborate derivatives and arylboronic acids with high regioselectivety at room temperature was discovered. The reaction shows exceptional functional group tolerance and broad substrate scope regarding both the quinoline derivatives and the arylboronic acids.

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.

Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines

A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.

Lewis acid-catalyzed borono-minisci reactions of arylboronic acids and heterocycles

A Lewis acid-catalyzed Minisci reaction between arylboronic acids and heterocycles has been developed. This radical-coupling reaction was demonstrated employing several different heterocycles as well as electron-rich arylboronic acids. Quinoline substrates afforded modest regioselectivity for substitution at the 4-position under the reaction conditions, in contrast to previously reported Br?nsted acid-mediated reactions with quinoline substrates that favored substitution at the 2-position.

Regioselective synthesis of 3-bromoquinoline derivatives and diastereoselective synthesis of tetrahydroquinolines via acid-promoted rearrangement of arylmethyl azides

Regioselective synthesis of 3-bromoquinoline derivatives was achieved via a formal [4 + 2]-cycloaddition between N-aryliminium ion, generated from arylmethyl azides, and 1-bromoalkynes. This method could also be applied to other quinoline derivatives using appropriate alkynes. Moreover, the current strategy could be utilized for the diastereoselective synthesis of tetrahydroquinoline derivatives employing alkenyl substrates in good to excellent yields.

QUINOLINE DERIVATIVES AS ANTIBACTERICAL AGENTS

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