14428-50-3

Upstream product

• 115307-35-2 N-<(4-methoxyphenyl)methylene>-2-(2-propenyl)benzenamine 
• 116-11-0 2-Methoxypropene 
• 836-41-9 p-methoxybenzylidene-phenylamine 
• 634-47-9 2-chloro-4-methylquinoline 
• 1196-39-0 4-methylisoquinoline 
• 104-94-9 4-methoxy-aniline 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 5720-07-0 4-methoxyphenylboronic acid 
• 4053-40-1 4-methylquinoline 1-oxide 
• 52562-19-3 2-isopropenylaniline 
• 123-11-5 4-methoxy-benzaldehyde 
• 1433772-22-5 N'-(1-(2-aminophenyl)ethylidene)-4-methylbenzenesulfonohydrazide 
• 768-60-5 4-methoxyphenylacetylen 
• 551-93-9 2-aminoacetophenone 

Downstream Products

• 135808-65-0 2-(4-methoxyphenyl)-4-quinolinecarboxaldehyde 

Relevant academic research and scientific papers

Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines

Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO3 was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ? induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.

Direct C-H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents

A direct and convenient method for the C-H arylation and alkylation of electron-deficient N-heteroarenes with readily available organozinc reagents has been developed. This transformation could be readily performed in the absence of a transition-metal catalyst and external oxidants, affording a wide range of substituted heteroarenes with good functional group tolerance in good to excellent yields. The developed simple protocol is scalable to the gram level and suitable for late-stage modification of bioactive molecules and drugs.

Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines

Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).

Rh(iii)-catalyzed alkynylation: Synthesis of functionalized quinolines from aminohydrazones

Rhodium-catalyzed, chemo- and regioselective synthesis of functionalized quinolines using 2-aminohydrazones and terminal alkynes has been described. The reaction is oxidant/base-free and tolerates a wide variety of functional groups and has been successfu

Iron-Catalyzed Aerobic Dehydrogenative Kinetic Resolution of Cyclic Secondary Amines

A nonenzymatic iron-catalyzed dehydrogenative kinetic resolution of cyclic secondary amines using air as an oxidant has been reported. The economical and practical method is applicable to a series of cyclic benzylic amines, including 5,6-dihydrophenanthridines and 1,2-dihydroquinolines, with diverse functional groups at the α position in high yields with excellent enantioselectivities. The direct dehydrogenative kinetic resolution of advanced intermediates of bioactive molecules that are difficult to access using existing catalytic asymmetric synthetic strategy was also demonstrated.

Direct arylation for the synthesis of 2-arylquinolines from N-methoxyquinoline-1-ium tetrafluoroborate salts and arylboronic acids

A rapid and direct arylation reaction of N-methoxyquinoline-1-ium tetrafluoroborate derivatives and arylboronic acids with high regioselectivety at room temperature was discovered. The reaction shows exceptional functional group tolerance and broad substrate scope regarding both the quinoline derivatives and the arylboronic acids.

Quantitative structure activity relationship and biological activity studies of 4-methyl-2-(4-substituted phenyl)quinoline derivatives

Quantitative structure activity relationship (QSAR) studies of some 4-methyl-2-(4-substituted phenyl)quinoline derivatives were carried out to determine their predicted biological activities. Numbers of descriptors were tested to adjudge a quantitative correlation between activity and structural features using training set and test set. Significant correlation was observed between activities and descriptors. The results were interpreted on the basis of linear regression analysis. Experimental antibacterial activities of the test set compounds were determined. The predicted biological activities generated by QSAR model were compared with the experimental antibacterial activities. The concurrence between the predicted and experimental biological activities validates the QSAR model. Thus, it can be concluded that the model under the present investigation can be applied for predicting the unknown biological activities of structurally similar molecules.

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

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.

Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines

An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates was developed for the synthesis of 2,4-disubstituted quinolines in moderate to good yields with good functional group compatibilities. Preliminary mechanistic studies suggest a plausible iron-catalyzed C-H activation process under external-oxidant-free conditions.