5659-33-6

Upstream product

• 2311-91-3 monoperoxyphthalic acid 
• 612-96-4 2-Phenylquinoline 
• 1613-37-2 Quinoline N-oxide 
• 108-86-1 bromobenzene 
• 53744-31-3 2-nitrochalcone 
• 634606-85-2 3-hydroxy-3-(2-nitrophenyl)-1-phenylpropane-1-one 
• 100-34-5 benzene diazonium chloride 
• 66003-76-7 Diphenyliodonium triflate 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 91-22-5 quinoline 
• 98-80-6 phenylboronic acid 
• 62-53-3 aniline 
• 100-63-0 phenylhydrazine 
• 3297-64-1 2-carboxyquinoline N-oxide 

Downstream Products

• 87732-10-3 3H-3-methoxyallyl-3-methoxycarbonyl-2-phenyl-1-benzazepine 
• 612-96-4 2-Phenylquinoline 
• 25365-71-3 2-phenyl-1H-indol-3-carboxaldehyde 
• 5855-50-5 3-hydroxy-2-phenylquinoline 
• 1620100-81-3 8-iodo-2-phenylquinoline N-oxide 
• 1620101-21-4 8-(4-methylphenylsulfonamido)-2-phenylquinoline N-oxide 

Relevant academic research and scientific papers

N2H4-H2O Enabled Umpolung Cyclization of o-Nitro Chalcones for the Construction of Quinoline N-Oxides

Umpolung is a unique strategy which converts the property of an atom into the opposite one. An efficient and general method for the construction of quinoline N-oxides via umpolung of carbonyl groups was developed from ortho-nitro chalcones and hydrazine i

Fluorine-containing 2,3-diaryl quinolines as potent inhibitors of methicillin and vancomycin-resistant Staphylococcus aureus: Synthesis, antibacterial activity and molecular docking studies

Drug resistant bacteria pose a major health concern and affect a large section of global population. Antibacterial drug discovery has stagnated owing to multiple factors including unattractive returns for major pharmaceutical companies. Thus, discovery of effective antibacterial drugs against drug-resistant bacteria is an urgent unmet need affecting healthcare systems globally. In this study, fluorine-containing 2,3-diarylquinolines (4a-l) and non-fluorinated analog 4m were synthesized utilizing environmentally benign chemistry of arenediazonium salts and arynes for regioselective installation of aryl groups at C-2 and C-3 positions, respectively. In vitro antibacterial evaluation against various Gram-negative and Gram-positive bacteria revealed inhibitory activity of majority of these compounds against Gram-positive S. aureus ATCC 29213. Compounds 4e, 4i, 4j and 4l were most potent inhibitors with MIC values of 10.95?24.0 μM. None of the compounds inhibited Gram-negative bacteria. 4e, 4i and 4l also displayed low levels of cytotoxicity against Vero cells, therefore, offering high safety profiles. Importantly, 4e, 4i and 4l exhibited equipotent inhibition of Methicillin and Vancomycin-resistant S. aureus, rendering them potential hits for further development. Molecular docking studies with topoisomerase II DNA gyrase demonstrated significant interactions of these inhibitors with target protein, which provided valuable insights into their potent antibacterial activity.

Co(III)-Catalyzed C-H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions

A cobalt(III)-catalyzed C-8 selective C-H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines. Furthermore, the developed catalytic method is also applicable for C-7 amidation of N-pyrimidylindolines and ortho-amidation of benzamides.

Visible-light-promoted c2 selective arylation of quinoline and pyridine n-oxides with diaryliodonium tetrafluoroborate

A protocol of visible-light-promoted C2 selective arylation of quinoline and pyridine N-oxides, with diaryliodonium tetrafluoroborate as an arylation reagent, using eosin Y as a photocatalyst for the construction of N-heterobiaryls was presented. This met

Preparation method of 2- aryl substituted quinoline nitrogen oxide compound

The preparation method 2 - of, aryl-substituted quinoline nitrogen oxide is 2 - The method, according to the present invention provides,aryl-substituted quinoline nitrogen oxide compound, in a nitrogen atmosphere at room temperature, The method for prepar

RhIII-Catalyzed Straightforward Synthesis of Benzophenanthroline and Benzophenanthrolinone Derivatives using Anthranils

An efficient pot-economic and step-economic RhIII-catalyzed site-selective direct amination/annulation strategy was developed for the synthesis of benzophenanthroline derivatives using quinoline N-oxides and anthranils. The method was further extended to the synthesis of nitrogen-containing extended π-conjugated benzophenanthrolinone derivatives. Late-stage functionalizations of cinchonidine and cinchophen derivatives and synthesis of a bioactive quinolino-indole were achieved.

Rh/O2-Catalyzed C8 Olefination of Quinoline N-Oxides with Activated and Unactivated Olefins

The rhodium/O2 system-catalyzed distal C(sp2)-H olefination of quinoline N-oxides is developed. Molecular oxygen has been explored as an economic and clean oxidant, an alternative to inorganic oxidants. A wide substrate scope with respect to quinoline N-oxides and olefins (activated acrylates and styrenes; unactivated aliphatic olefins) demonstrates the robustness of the developed catalytic method. Interestingly, 2-substituted quinoline N-oxides also afforded good yields of the corresponding C8-olefinated products. Kinetic isotope studies and deuterium-labeling experiments have been performed to understand the preliminary mechanistic pathway. The applicability of the developed method is demonstrated by utilizing natural product-derived substrates and by converting the C8-olefinated quinoline N-oxides into various other useful molecules.

Catalyst-Free Synthesis of 2-Anilinoquinolines and 3-Hydroxyquinolines via Three-Component Reaction of Quinoline N-Oxides, Aryldiazonium Salts, and Acetonitrile

A rapid microwave-assisted, catalyst-free, three-component synthesis of various 2-anilinoquinolines from quinoline N-oxides and aryldiazonium salts in acetonitrile under microwave irradiation is reported. This reaction utilizes acetonitrile as a single nitrogen source and involves the formation of two new C-N bonds via the formal [3 + 2] cycloaddition reaction. In the case of 2-substituted quinolines, 3-hydroxyquinoline was observed as the main product via a 1,3 shift of the oxygen atom from N-oxide to the C3 position of quinolines.

Electrochemical Deoxygenation of N-Heteroaromatic N -Oxides

An electrochemical method for the deoxygenation of N-heteroaromatic N -oxide to give the corresponding N-heteroaromatics has been developed. Several classes of N-heterocycles such as pyridine, quinoline, isoquinoline, and phenanthridine are tolerated. The electrochemical reactions proceed efficiently in aqueous solution without the need for transition-metal catalysts and waste-generating reducing reagents.

Rh(III)-Catalyzed C(8)-H Functionalization of Quinolines via Simultaneous C-C and C-O Bond Formation: Direct Synthesis of Quinoline Derivatives with Antiplasmodial Potential

Here, a facile and efficient protocol for the synthesis of 3-hydroxyquinolin-8-yl propanoates via Rh(III)-catalyzed C(8)-H activation of 2-substituted quinolines has been developed. The reaction proceeds via C(8)-H activation, functionalization with acrylates, followed by intramolecular migration of the oxygen atom from quinoline N-oxides to the acrylate moiety. In this approach, N-oxide plays a dual role of a traceless directing group as well as a source of an oxygen atom for hydroxylation. This catalytic method involves simultaneous formation of new C-C and C-O bonds and is applicable only for C2-substituted quinolines. A catalytically competent five-membered rhodacycle has been characterized, thus revealing a key intermediate in the catalytic cycle. In silico docking studies against Falcipan-2 have revealed that 3a, 3b, 3g, and 3m have better scores. In vitro evaluation of selected compounds against CQ-sensitive pf3D7 and CQ-resistant pfINDO strains provided evidence that 3d (IC50 13.3 μM) and 3g (IC50 9.5 μM) had good promise against Plasmodium falciparum in the in vitro culture. Compound 3g was found to be the most potent on the basis of both in vitro antiplasmodial activity [IC50 9.5 μM (Pf3D7) and 11.9 μM (PfINDO), resistance index 1.25] and in silico studies.