159090-73-0

Upstream product

• 578-66-5 8-amino quinoline 
• 403-43-0 4-fluorobenzoyl chloride 
• 456-22-4 4-Fluorobenzoic acid 
• 312503-18-7 2-hydroxy-N-(quinolin-8-yl)benzamide 
• 129476-63-7 2,2,2-trifluoro-N-(quinolin-8-yl)acetamide 
• 352-13-6 4-flourophenylmagnesium bromide 
• 134-32-7 1-amino-naphthalene 

Downstream Products

• 1404616-70-1 N-(2,6-di(trifluoromethylthio)-4-fluorobenzoyl)-8-aminoquinoline 
• 1647073-80-0 4-fluoro-2-nitro-N-(quinolin-8-yl)benzamide 
• 1428858-67-6 2-methyl-4-fluoro-N-(quinolin-8-yl)benzamide 

Relevant academic research and scientific papers

Copper-catalyzed phosphorylation of sp2 C-H bonds

The phosphorylation of the ortho C-H bonds in benzamides containing an 8-aminoquinoline moiety as a bidentate directing group with H-phosphonates using copper as a catalyst under mild temperature conditions is described. This method shows high functional group compatibility and selectively gives mono-substituted products. This journal is

Probing the Noninnocent π-Bonding Influence of N-Carboxyamidoquinolate Ligands on the Light Harvesting and Redox Properties of Ruthenium Polypyridyl Complexes

Electronic and photophysical characterization is presented for a series of bis-heteroleptic [Ru(bpy)2(R-CAQN)]+ complexes where CAQN is a bidentate N-(carboxyaryl)amidoquinolate ligand and the aryl substituent R = p-tolyl, p-fluorobenzene, p-trifluoromethylbenzene, 3,5-bis(trifluoromethyl)benzene, or 4-methoxy-2,3,5,6-tetrafluorobenzene. Characterized by a strong noninnocent Ru(dπ)-CAQN(π) bonding interaction, density functional theory (DFT) analysis is used to estimate the contribution of both atomic Ru(dπ) and ligand CAQN(π) manifolds to the frontier molecular orbitals of these complexes. UV-vis absorption and emission studies are presented where the noninnocent Ru(dπ)-CAQN(π) bonding scheme plays a major role in defining complex electronic and photophysical properties. Oxidation potentials are tuned over a range of 0.92 V with respect to the [Ru(bpy)3]2+ reference system, hereafter referred to as 12+, by varying the degree of R-CAQN fluorination while maintaining consistently strong and panchromatic visible absorption properties. Electron paramagnetic resonance (EPR) spectroscopy is employed to experimentally map delocalization of the unpaired electron/electron-hole within the delocalized Ru(dπ)-CAQN(π) singly occupied valence molecular orbital of the one-electron oxidized complexes. EPR data is complemented experimentally by UV-vis-NIR spectroelectrochemistry, and computationally by molecular orbital Mulliken contributions and spin-density analysis. It is ultimately demonstrated that the CAQN ligand framework provides a simple yet broad synthetic platform in the design of redox-active transition metal chromophores with a range of electronic and spectroscopic characteristics hinting at the diversity and potential of these complexes toward photochemical and catalytic applications.

Metal-Free Electrochemical Oxidative Dihalogenation of Quinolines on the C5 and C7 Positions Using N-Halosuccinimides

An efficient and convenient method for electrochemically oxidative dichlorination or dibromination of 8-aminoquinolines on C5 and C7 positions using N-halosuccinimides (NCS and NBS) as the halogen source was described. Substrates with various functional g

Direct oxytosylation of 8-amidoquinolines by koser's reagent: An efficient strategy for 5-substituted 8-amidoquinolines

A metal-free remote oxytosylation of 8-amidoquinolines has been achieved using Koser's reagent to produce 5-tosyloxy-8-amidoquinolines in good yields. This method is compatible with various functional groups present on the aromatic ring.

Regioselective remote C–H fluoroalkylselenolation of 8-aminoquinolines

Herein, the direct C-5 fluoroalkylselenolation of 8-aminoquinolines is described. The Pd-catalyzed reaction is performed with the in situ generated fluoroalkylselenyl chloride and various 8-aminoquinoline amides or sulfonamides. The desired products were

C-H Amidation and Amination of Arenes and Heteroarenes with Amide and Amine using Cu-MnO as a Reusable Catalyst under Mild Conditions

An atom-economical and efficient route for the direct amidation and amination of aryl C-H bonds using our synthesized recyclable heterogeneous Cu-MnO catalyst is reported here. The direct C-H amidation was carried out using a simple amide without any prea

C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane

An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale

Nickel-mediated C(sp2)-H amidation in synthesis of secondary sulfonamides via sulfonyl azides as amino source

In this paper, Ni(II)- Catalyzed ortho-amidation of C(sp2)-H bond with sulfonyl azides directed by (quinolin-8-yl) amine (AQ-amine) is described. The method provides a straightforward method for the synthesis of sulfonamides from available sulfonyl azides via the transition-metal-catalyzed C(sp2)-N bond forming reaction. The amidation reactions exhibit high functional group compatibility, which might proceed a Ni(III)/Ni(I) catalytic cycle. We also applied sulfonamide compound in OLEDs, which exhibits the certain application potential in OLEDs field.

Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.

Copper-Catalyzed Electrochemical Selective Bromination of 8-Aminoquinoline Amide Using NH4Br as the Brominating Reagent

A simple and mild protocol for copper-catalyzed bromination of quinoline at the C5 site of quinoline by anodic oxidation was developed, affording the desired remote C-H activation products with isolated yields of up to about 90%. The reaction proceeds wit