36710-31-3

Upstream product

• 18457-79-9 2-cyanoquinoline N-oxide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1613-37-2 Quinoline N-oxide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 3297-64-1 2-carboxyquinoline N-oxide 
• 623-12-1 4-chloromethoxybenzene 
• 104-94-9 4-methoxy-aniline 
• 16032-40-9 2-(4-methoxyphenyl)quinoline 
• 5720-07-0 4-methoxyphenylboronic acid 
• 3471-32-7 4-Methoxyphenylhydrazine 

Downstream Products

• 16032-40-9 2-(4-methoxyphenyl)quinoline 

Relevant academic research and scientific papers

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.

KMnO4-mediated direct selective radical cross-coupling: An effective strategy for C2 arylation of quinoline N-oxide with arylboronic acids

Direct C[sbnd]H functionalization of quinoline N-oxides with arylboronic acids is achieved using KMnO4 as the sole and efficient oxidative system. This method provides an efficient protocol to construct regioselectively 2-arylquinoline N-oxides

KMnO4-mediated direct C2-selective C?H arylation of quinoline N-oxides with aromatic hydrazines

An efficient protocol for the synthesis of 2-arylquinoline N-oxides has been developed via KMnO4-mediated cross-coupling reaction of quinoline N-oxides with aromatic hydrazines in moderated to good yields. The reactions proceeded efficiently over a broad range of substrates with excellent regioselectivity and functional group tolerance.

Cu(OAc)2-catalyzed direct radical C2 arylation of quinoline N-oxide with arylamines

A Cu(OAc)2-catalyzed synthesis of 2-arylquinoline N-oxides with easily available arylamines is described. The main features of this reaction are mild reaction conditions, high functional-group tolerance, excellent regioselectivity, and good to excellent yields. This procedure is mild, operationally simple, and constitutes a greener approach to the arylation of quinoline N-oxides.

Pd-catalyzed decarboxylative cross-coupling of 2-carboxyazine N-oxides with various (hetero)aryl halides

Decarboxylative cross-coupling reactions of substituted 2-carboxyazine N-oxides, with a variety of (hetero)aryl halides, by bimetallic Pd 0/CuI and Pd0/AgI catalysis are reported. Two possible pathways, a conven

Chemoselective synthesis of quinoline N-oxides from 3-(2-nitrophenyl)-3- hydroxypropanones

The reaction of 3-(2-nitrophenyl)-3-hydroxypropanones with Zn/NH 4Cl gave the corresponding quinoline N-oxides in 80-90% yields. The reaction initiated the reduction of nitro group to afford the corresponding hydroxylamine, which intramolecularly condensed and followed by dehydration to give quinoline N-oxide. Although treatment of 2-nitrochalcone with Zn/NH 4Cl in EtOH/H2O resulted in the formation of quinoline N-oxide in low yield, the reaction of 2-nitrochalcone with Sn/NH4Cl in refluxing EtOH/H2O afforded quinoline N-oxide in 80% yield.

Quinoline Nitroxide Radicals. Ipso-Attack in the Reaction between 2-Methoxy and 2-Cyanoquinoline N-oxide, and Phenylmagnesium Bromide

2-Methoxy and 2-cyanoquinoline N-oxide, when treated with phenylmagnesium bromide, undergo a nucleophilic ipso-attack at C-2, yielding, by elimination of methoxymagnesium bromide or cyanomagnesium bromide, the corresponding 2-phenylquinoline N-oxides, which react with the excess of Grignard reagents forming 2,2-diphenylquinoline 1-oxyls.Even when the methoxy and cyano groups are in position 4, the attack by the Grignard reagent takes place at C-2 giving 2-phenylquinolines and 2-phenylquinoline N-oxides by elimination by hydroxymagnesium bromide and bromomagnesium hydride, respectively; the formation of 2,2-diphenylquinoline 1-oxyls in these reactions is discussed.