21280-55-7

Upstream product

• 34241-39-9 azobisisobutyronitrile 
• 10349-38-9 p-methoxyphenylisonitrile 
• 536-74-3 phenylacetylene 
• 30034-43-6 7-methoxy-4-phenyl-1, 2-dihydroquinolin-2-one 
• 67-68-5 dimethyl sulfoxide 
• 536-90-3 m-Anisidine 
• 16717-64-9 1-azidostyrene 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 50-00-0 formaldehyd 
• 98-86-2 acetophenone 
• 1217436-59-3 N-(3-phenylprop-2-ynyl)-3-methoxyaniline 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 21280-45-5 3-((3-methoxyphenyl)amino)-1-phenylpropan-1-one 
• 78994-03-3 2-Chloro-3-m-anisyl-6-phenyl-3,4-dihydro-1,3,2-oxazaphosphorin-2-oxide 

Relevant academic research and scientific papers

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.

Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines

A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr, and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)2-catalyzed ring closure of these same alkynylanilines.

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.

Radical Annulations and Cyclisations with Isonitriles: the Fate of the Intermediate Imidoyl and Cyclohexadienyl Radicals

The reaction of 4-methoxyphenylisonitrile with phenylacetylene and AIBN produces a novel cyclopenta-fused quinoxalin through addition of 2-cyanoprop-2-yl radical to the alkyne; the resultinge vinyl radical attacks isonitrile to afford an imidoyl radical, which gives rise to a tandem 5-exo, 6-endo cyclisation.The whole process entails a new example of a rare 4 + 1 radical annulation.The cyanopropyl radical can also attack isonitrile to yield small amounts of quinolines deriving from 4 + 2 and 3 + 2 annulation between the resulting imidoyl radicals and phenylacetylene.The oxidation step leading to the final aromatic products involves the starting isonitrile, which is converted to an α-unsubstituted imidoyl radical and affords 2-unsubstituted quinolines.This behaviour was also found in cyclisations of biphenyl-2-ylisonitrile under various radical conditions.Finally, the title reaction gives small ammounts of an α,β-unsaturated nitrile, which can arise from a spirocyclohexadienyl radical through fragmentation and subsequent β-scission of the resulting iminyl.This could be the first, direct evidence of the intermediacy of iminyl radicals in the rearrangements of the spirocyclohexadienyls obtained by 3 + 2 annulation between imidoyl radicals and alkynes.

Heteroaryl quinolines as inhibitors of leukotriene biosynthesis

Compounds having the formula I: STR1 are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.

Synthesis and Reactions of 3,6-Diaryl-3,4-dihydro-1,3,2-oxazaphosphorin-2-oxides

Aryl β-arylaminoethyl ketones (1), when reacted with phosphorus oxychloride followed by treatment with triethylamine, afford 3,6-diaryl-2-chloro-3,4-dihydro-1,3,2-oxazaphosphorin-2-oxides (3a-u), a hitherto unreported ring system.The oxazaphosphorin (3q), viz. 2-chloro-3-m-anisyl-6-phenyl-3,4-dihydro-1,3,2-oxazaphosphorin, is converted into 7-methoxy-4-phenylquinoline on keeping.This transformation is specific to 3q since other oxazaphosphorins fail to give the quinoline derivative.