362650-17-7

Upstream product

• 75-16-1 methylmagnesium bromide 
• 145297-31-0 7-chloro-(4-phenyl)quinoline 
• 104-55-2 3-phenyl-propenal 
• 108-44-1 1-amino-3-methylbenzene 
• 2579-22-8 Phenylpropargyl aldehyde 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 13194-69-9 2-iodo-5-methylaniline 
• 50-00-0 formaldehyd 
• 98-86-2 acetophenone 
• 67-68-5 dimethyl sulfoxide 
• 536-74-3 phenylacetylene 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 16717-64-9 1-azidostyrene 
• 298-12-4 Glyoxilic acid 

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.

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.

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.

Direct Assembly of 4-Substituted Quinolines with Vinyl Azides as a Dual Synthon via C=C and C-N Bond Cleavage

An unprecedented Zn-promoted selective cleavage of vinyl azides for the synthesis of 4-substituted quinolines is developed. In this conversion, vinyl azides function as a dual synthon via C=C and C-N bond cleavage with two C=C bonds and one C=N bond formation in a one-step manner. The reaction is appreciated for its readily accessible substrates, high step economy, mild conditions, and use of air as the sole oxidant.

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.

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.

Silver-catalyzed oxidative coupling of aniline and ene carbonyl/acetylenic carbonyl compounds: An efficient route for the synthesis of quinolines

An efficient silver-mediated coupling of aniline with ene carbonyl/acetylenic carbonyl compounds for the synthesis of quinolines is reported. The transformation is effective for a broad range of substrates, thus enabling the expansion of substituent architectures on the heterocyclic framework. The electronic properties of the substituents on the amine have been investigated. It was found that molecules with both electron-donating and electron-withdrawing substituents were suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields. The use of a single catalytic system to mediate chemical transformations in a synthetic operation is important for the development of new atom-economic strategies and this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.

Novel pharmaceutical compounds

The instant invention provides compounds of Formula I which are leukotriene biosynthesis inhibitors. Compounds of Formula I are useful as anti-atherosclerotic, anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.

SUBSTITUTED QUINOLINES AS INHIBITORS OF LEUKOTRIENE BIOSYNTHESIS

The instant invention provides compounds of Formula (I) which are leukotriene biosynthesis inhibitors. Compounds of Formula (I) are useful as anti-atherosclerotic, anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.

A new synthesis of 4-phenylquinolines by reaction of 2-(α-bromobenzyl)oxiranes with aniline derivatives

Several 4-phenylquinoline derivatives were synthesized by reaction of (2R*,1′R*)-2-(α-bromobenzyl)oxiranes (1a) with aniline derivatives, and the following treatment of the formed 3-hydroxy-4-phenyl-1,2,3,4-tetrahydroquinolines (2) with the Rydon reagent, and potassium t-butoxide and air oxidation.