3813-92-1

Upstream product

• 144709-08-0 2-(4-methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 768-60-5 4-methoxyphenylacetylen 
• 1256842-42-8 ethyl 3-cyano-3-phenylamino-3-(4-methoxyphenyl)propanoate 
• 1200055-82-8 1-(2-aminophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one 
• 2142-69-0 2-bromophenyl methyl ketone 
• 33768-41-1 N-(2-acetyl-phenyl)-4-methoxy-benzamide 
• 577-59-3 2-acetylnitrobenzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 118-48-9 isatoic anhydride 
• 1357394-80-9 1-(2-bromophenyl)-3-(4-methoxyphenyl)-prop-2-yn-1-ol 
• 1203669-21-9 1-(2-bromophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 246181-55-5 1-methyl-2-(4’-methoxyphenyl)-1H-4-quinolone 
• 1375678-88-8 C₁₆H₁₂ClNO₂ 
• 21202-79-9 4-chloro-2-(4-methoxy)phenyl quinoline 
• 502841-05-6 4-chloro-3-bromo-2-(4-methoxyphenyl)quinoline 
• 876460-09-2 3-iodo-2-(4'-methoxyphenyl)-1-methylquinolin-4(1H)-one 
• 502841-12-5 3-bromo-2-(4'-methoxyphenyl)quinolin-4(1H)-one 
• 882866-44-6 3-iodo-2-(4'-methoxyphenyl)-quinolin-4(1H)-one 

Relevant academic research and scientific papers

QUINOLONE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF

The present invention relates to quinolones of formula (I) and process for its preparation by amine insertion into aryl-ynones thereof. [Formula I] The invention further relates to the process to obtain the natural products such as: graveoline, graveolinine, pseudane IV, pseudane VII, pseudane VIII and pseudane XII. The invention also describes the process for the total synthesis of waltherione F in concise approach from the quinolone synthesized. [Formula II]

Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates

Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.

In quest of small-molecules as potent non-competitive inhibitors against influenza

A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.

An Efficient Synthesis of (1-Methyl)-2-phenyl-4-quinolones from (N-Methyl)isatoic Anhydride

The acyl substitution of (N-methyl)isatoic anhydride with N,O-dimethylhydroxylamine hydrochloride in CH3CN gave N-methoxy-N-methyl 2-(N-methyl)aminobenzamide, which was treated with ethynyllithium reagents to afford 1-[2-(N-methyl)amino]-3-phen

Access to 2-Alkyl/Aryl-4-(1 H)-Quinolones via Orthogonal "nH3" Insertion into o-Haloaryl Ynones: Total Synthesis of Bioactive Pseudanes, Graveoline, Graveolinine, and Waltherione F

An efficient one-pot synthesis of 4-(1H)-quinolones through an orthogonal engagement of diverse o-haloaryl ynones with ammonia in the presence of Cu(I), involving tandem Michael addition and ArCsp2-N coupling, is presented. The substrate scope of this convenient protocol, wherein ammonium carbonate acts as both an in situ ammonia source and a base toward diverse 2-substituted 4-(1H)-quinolones, has been mapped and its efficacy validated through concise total synthesis of bioactive natural products pseudanes (IV, VII, VIII, and XII), graveoline, graveolinine, and waltherione F.

Safe synthesis method of quinolone compounds using solid carbonyl source

The invention discloses a safe synthesis method of quinolone compounds using a solid carbonyl source, 2-iodoaniline compounds and terminal alkynes as substrates, palladium acetate as a catalyst, 4,5-diphenylphosphine-9,9-dimethylxanthene as a ligand, chromium hexacarbonyl as the solid carbonyl source are used, triethylamine activates the solid carbonyl source to release CO in an air atmosphere, and the quinolone compounds are efficiently synthesized by a one-pot method. The in-situ slow release of the CO from the chromium hexacarbonyl activated by air oxidation is realized, the kinetics of carbon-carbon bond cross-coupling reaction is effectively matched and catalyzed, and a safe and efficient carbonylation cyclization process is realized. The catalytic reaction system is characterized inthat the triethylamine and piperazine are compounded and coordinated, an effective series connection of carbonylation carbon-carbon coupling and cyclization process is constructed, and ternary cyclization of the 2-iodoaniline compounds, the terminal alkynes and the CO is realized. The safe synthesis method has the advantages of simple and safe operation, high reaction efficiency, mild conditions and good substrate applicability, and can be widely used for' one-pot' synthesis of the quinolone compounds.

Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles

Reductive ring transformation of 3-substituted 5-(2-nitrophenyl)isoxazoles, readily accessible via 1,3-dipolar cycloaddition of 2-ethinylnitrobenzene with nitrile oxides, opens a novel access to 2-substituted quinolin-4-ones. Nickel boride, generated in situ from nickel chloride and sodium borohydride, allows, via simultaneous reduction of the nitro group and reductive cleavage of the isoxazole ring, the one-step conversion into the target quinolin-4-ones. This protocol tolerates various functional groups, except olefins, and thus is complementary to the reductive ring transformation with iron/acetic acid, which predominantly tolerates olefins.

Method for preparing quinolones compound by using pentacarbonyl iron as CO release source

The invention discloses a method for preparing quinolones compound by using pentacarbonyl iron as a CO release source. In this method, iron pentacarbonyl is used as a CO release source, and palladiumacetate is used as a catalyst, potassium phosphate and piperazine are used as a base, and acetonitrile is used as a solvent to couple a 2-iodoaniline compound with a terminal alkyne under mild conditions to obtain the quinolones compound. The preparation method has the advantages of simple operation, mild reaction conditions, less catalyst use, less CO release source use, low toxicity, lower cost,wide substrate applicability, and high target compound yield, and the method can be widely used for the preparation of natural quinolones compound.

2-aryl-4-quinolone derivative as well as preparation method and application thereof

The invention discloses a 2-aryl-4-quinolone derivative as well as a preparation method and an application thereof. The 2-aryl-4-quinolone derivative has the structure shown in formula (I) in the description, wherein R1 is independently selected from one or more of H, C1-C5 alkyl, halogen or C1-C5 alkoxy, and R2 is independently selected from one or more of H, C1-C5 alkyl, CF3, halogen or C1-C5 alkoxy. Test results show that the 2-aryl-4-quinolone derivative has good antibacterial activity and can be used as an antibacterial agent.

Carbonylative Sonogashira annulation sequence: One-pot synthesis of 4-quinolone and 4H-chromen-4-one derivatives

Carbonylative Sonogashira annulation sequence for one pot synthesis of 4-quinolone and 4H-chromen-4-one has been developed in presence of Pd-NHC catalyst. Substituted 2-iodoaniline and 2-iodophenol independently underwent in the carbonylative Sonogashira