138386-76-2

Upstream product

• 612-62-4 2-Chloroquinoline 
• 104-94-9 4-methoxy-aniline 
• 1613-37-2 Quinoline N-oxide 
• 10076-13-8 N,N'-bis(4-methoxyphenyl)carbodiimide 
• 1436-43-7 quinoline-2-carbonitrile 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 138386-53-5 C₂₆H₂₂NP 
• 5416-93-3 4-Methoxyphenyl isocyanate 
• 3867-18-3 2-vinylaniline 

Relevant academic research and scientific papers

Site-Selective Deoxygenative Amination of Azine N-Oxides with Carbodiimides under Catalyst-, Activator-, Base-, and Solvent-Free Conditions

An operationally simple method for synthesizing 2-amino azines via [3+2] dipolar cycloaddition of azine N-oxide with carbodiimide has been demonstrated. The reaction can proceed smoothly under simple heating conditions without any transition metal catalyst, activator, base, and solvent. This transformation demonstrates a broad substrate scope and produces CO2 as the only co-product. The applicability of this method is highlighted by the late-stage modification of bioactive molecules, including quinine, (±)-α-tocopherol, and tryptamine modified quinoline.

Heteroarylation method of amine

The invention discloses a heteroarylation method of amine, and the method comprises the following steps of: mixing an amine compound, heteroaromatic hydrocarbon, a photocatalyst and an organic solventto obtain a solution A; and in an inert gas atmosphere, irradiating the solution A with visible light, and carrying out reaction to obtain a heteroarylated product of amine. According to the method,under mild conditions, free radical coupling of amine compounds and heteroaromatic compounds is efficiently achieved through visible light irradiation, and various heteroarylamines are synthesized. The method has good functional group compatibility and high regioselectivity, can be further applied to later modification of bioactive molecules, and shows a good industrial application prospect.

Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis

Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.

A mild and metal-free synthesis of 2- And 1-alkyl/aryl/dialkyl-aminoquinolines and isoquinolines

A simple synthetic strategy has been developed for the synthesis of 2- and 1-alkyl/aryl/dialkylaminoquinolines and isoquinolines from the easily available quinoline and isoquinoline-N-oxides, different amines, triflic anhydride as activating agent and ace

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.

Synthesis and anti-HCV activity evaluation of anilinoquinoline derivatives

Hepatitis C virus (HCV) infection is a main cause of chronic liver disease, leading to liver cirrhosis and hepatocellular carcinoma (HCC). The objective of our research was to develop effective agents against viral replication. Here, we have synthesized a

Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists

Quinoline, isoquinoline, quinoxaline, and quinazoline derivatives were synthesized using microwave-assisted synthesis and their CB1/CB2 receptor activities were determined using the [35S]GTPγS binding assay. Most of the prepared quinoline, isoquinoline, and quinoxalinyl phenyl amines showed low-potency partial CB2 receptor agonists activity. The most potent CB2 ligand was the 4-morpholinylmethanone derivative (compound 40e) (-log EC 50 = 7.8; Emax = 75%). The isoquinolin-1-yl(3- trifluoromethyl-phenyl)amine (compound 26c) was a high efficacy CB2 agonist (-log EC50 = 5.8; Emax = 128%). No significant CB1 receptor activation or inactivation was shown in these studies, except 40e, which showed weak CB1 agonist activity (CB1 -log EC50 = 5.0). These ligands serve as novel templates for the development of selective CB2 receptor agonist.