141075-44-7

Upstream product

• 58867-43-9 4-methyl-1,5-diphenyl-2,3-dihydropyrrole-2,3-dione 
• 63478-10-4 2-(2'-anilinyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 93-55-0 1-phenyl-propan-1-one 
• 1196-28-7 2'-Aminopropiophenon 
• 100-51-6 benzyl alcohol 
• 108-88-3 toluene 
• 551-93-9 2-aminoacetophenone 
• 16714-26-4 1-(2-azido-phenyl)-ethanone 
• 1220997-84-1 2-(2-azidophenyl)-4-phenylbut-3-yn-2-ol 
• 351342-74-0 N-(2-propionylphenyl)benzamide 
• 201230-82-2 carbon monoxide 
• 14752-72-8 1,N-Diphenylpropanimine 
• 154010-87-4 1-[2-(benzylamino)phenyl]propan-1-one 
• 100-39-0 benzyl bromide 

Downstream Products

• 56858-10-7 1,3-dimethyl-2-phenylquinolin-4(1H)-one 
• 64495-56-3 4-chloro-3-methyl-2-phenylquinoline 

Relevant academic research and scientific papers

Biological activity of intervenolin analogs with a phenyl substituent

Intervenolin analogs with a phenyl substituent at the 2- or 3-position were synthesized. The compounds (3-11) showed weak or no inhibitory activity toward the growth of MKN-74 gastric adenocarcinoma cells, even in the presence or absence of the corresponding Hs738 stromal cells, whereas 2-substituted analogs exhibited selective anti-Helicobacter pylori activity. Introduction of a pendant side chain on the nitrogen alleviated their acute toxicity in mice. The 2-phenyl-substituted analogs are reasonable structural templates for structure-activity relationship studies toward the development of anti-H. pylori agents that do not affect human cells.

Microwave-induced molecular rearrangements. flash thermolysis in the gas-phase and in solution: Synthesis of quinolones and naphthyridones

3- and 4-Pyridyliminopropadienones were prepared by flash vacuum thermolysis of Meldrum's acid derivatives and characterized by low temperature IR spectroscopy. They react with dimethylamine to afford 1,5-, 1,6-, and 1,7-naphthyridones. The same naphthyri

One-Pot Synthesis of 4-Quinolone via Iron-Catalyzed Oxidative Coupling of Alcohol and Methyl Arene

Herein, we describe the iron(III)-catalyzed oxidative coupling of alcohol/methyl arene with 2-amino phenyl ketone to synthesize 4-quinolone. Alcohols and methyl arenes are oxidized to the aldehyde in the presence of an iron catalyst and di-tert-butyl peroxide, followed by a tandem process, condensation with amine/Mannich-type cyclization/oxidation, to complete the 4-quinolone ring. This method tolerates various kinds of functional groups and provides a direct approach to the synthesis of 4-quinolones from less functionalized substrates.

Gold-catalyzed cyclization of 1-(2′-Azidoaryl) propynols: Synthesis of polysubstituted 4-quinolones

An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-Azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-Activated triple bonds in a 6-endo-dig manner and subsequent gold-Assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.

From Ketones, Amines, and Carbon Monoxide to 4-Quinolones: Palladium-Catalyzed Oxidative Carbonylation

A novel method of palladium-catalyzed oxidative carbonylation of ketones, amines, and carbon monoxide for the synthesis of 4-quinolones has been developed. This protocol provides a straightforward route to construct useful 4-quinolone derivatives from ine

Direct synthesis of 2-aryl-4-quinolones via transition-metal-free intramolecular oxidative C(sp3)-H/C(sp3)-H coupling

A novel, metal-free oxidative intramolecular Mannich reaction was developed between secondary amines and unmodified ketones, affording a simple and direct access to a broad range of 2-arylquinolin-4(1H)-ones through C(sp3)-H activation/C(sp3)-C(sp3) bond formation from readily available N-arylmethyl-2-aminophenylketones, using TEMPO as the oxidant and KOtBu as the base.

Flash flow pyrolysis: Mimicking flash vacuum pyrolysis in a high-temperature/high-pressure liquid-phase microreactor environment

Flash vacuum pyrolysis (FVP) is a gas-phase continuous-flow technique where a substrate is sublimed through a hot quartz tube under high vacuum at temperatures of 400-1100 °C. Thermal activation occurs mainly by molecule-wall collisions with contact times in the region of milliseconds. As a preparative method, FVP is used mainly to induce intramolecular high-temperature transformations leading to products that cannot easily be obtained by other methods. It is demonstrated herein that liquid-phase high-temperature/high- pressure (high-T/p) microreactor conditions (160-350 °C, 90-180 bar) employing near- or supercritical fluids as reaction media can mimic the results obtained using preparative gas-phase FVP protocols. The high-T/p liquid-phase "flash flow pyrolysis" (FFP) technique was applied to the thermolysis of Meldrum's acid derivatives, pyrrole-2,3-diones, and pyrrole-2-carboxylic esters, producing the expected target heterocycles in high yields with residence times between 10 s and 10 min. The exact control over flow rate (and thus residence time) using the liquid-phase FFP method allows a tuning of reaction selectivities not easily achievable using FVP. Since the solution-phase FFP method does not require the substrate to be volatile any more -a major limitation in classical FVP-the transformations become readily scalable, allowing higher productivities and space-time yields compared with gas-phase protocols. Differential scanning calorimetry measurements and extensive DFT calculations provided essential information on pyrolysis energy barriers and the involved reaction mechanisms. A correlation between computed activation energies and experimental gas-phase FVP (molecule-wall collisions) and liquid-phase FFP (molecule-molecule collisions) pyrolysis temperatures was derived.

Microwave-assisted synthesis of polysubstituted 4-quinolones from deprotonated α-aminonitriles

The α-alkylation of deprotonated N-aryl-α-aminonitriles with α-bromoesters furnishes intermediates that can be cyclized to 4-quinolones upon microwave irradiation. Alternatively, base-induced dehydrocyanation of the alkylation products furnishes enaminoes

The novel reaction of ketones with o-oxazoline-substituted anilines

A variety of ketones react with o-oxazoline-substituted anilines in the presence of catalytic amount of p-toluenesulfonic acid in dry n-butanol to form 4-amino-substituted quinolines or 4-quinolones in fair to good yields.

A Nitroketene to Nitrile Oxide Transformation

2,3-Dihydropyrrole-2,3-diones 1 thermally extrude CO, giving imidoylketenes 2, which cyclise efficiently to 4-quinolones 3; however, the analogous nitro(imidoyl)ketene 5 eliminates CO2 and rearranges to the 3-oximino-3H-indole 9, presumably via an imidoyl