56947-80-9

Upstream product

• 108-85-0 1-bromocyclohexane 
• 143671-61-8 4-methylquinoline trifluoroacetate 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 110-82-7 cyclohexane 
• 626-62-0 Cyclohexyl iodide 
• 813-19-4 bis(tri-n-butyltin) 
• 41320-40-5 <<(methylthio)thiocarbonyl>oxy>cyclohexane 
• 138715-77-2 phenyl-λ³-iodanediyl dicyclohexanecarboxylate 
• 35448-12-5 2-(cyclohexyloxy)-2-oxoacetic acid 
• 98-89-5 Cyclohexanecarboxylic acid 
• 94-36-0 dibenzoyl peroxide 
• 10590-69-9 4-methylquinoline-2-carbonitrile 
• 105398-69-4 Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 
• 105398-76-3 ((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid; compound with 4-methyl-quinoline 

Downstream Products

• 106719-56-6 2-(cyclohexen-1′-yl)-4-methylquinoline 
• 4789-76-8 4-methyl-2-phenylquinoline 

Relevant academic research and scientific papers

Tris(trimethylsilyl)silane in the Alkylation of Heteroaromatic Bases with Alkyl Halides

Protonated heteroaromatic bases were easily alkylated via radical pathways using alkyl halides in the presence of tris(trimethylsilyl)silane under photochemical or thermal conditions.

Radical Alkylation of Heteroaromatic Bases with Polysilane Compounds

Alkyl halides were treated with protonated heteroaromatic bases in the presence of 1,1,1,3,3,3-hexamethyl-2,2-bis(trimethylsilyl)trisilane under photochemical conditions to give the corresponding alkylated heteroaromatic bases easily.The alkylation of pro

Photochemical Magnetic Field Effects of 4-Methyl-2-quinolinecarbonitrile

The irradiation of 4-methyl-2-quinolinecarbonitrile 1 in ethanol or cyclohexane resulted in the formation of 2-(1-hydroxyethyl)-4-methylquinoline 2 or 2-cyclohexyl-4-methylquinoline 3 in the yield of ca. 48 or 65percent.The effects of an external magnetic field upon the photosubstitution reaction were investigated in either the absence or presence of 1,3-pentadiene (triplet quencher).In the case of the photosubstitution reaction (1->2) in ethanol, the chemical yield of 2 increased quadratically with an increase in the field strength (magnetic field effect due to HFI-J mechanism).The addition of 1,3-pentadiene caused a complete disappearance of the Δg magnetic field effect.Thus, the formation of 2 at a zero field was concluded to occur from the S1-state via the singlet hydrogen-bonded radical pair.In the case of the photosubstitution reaction (1->3) in cyclohexane, the chemical yield of 3 decreased steeply upon the application of a magnetic field of 40mT (magnetic field effect due to HFI mechanism) and a further increase in the field strength resulted in a quadratic increase in the yield (magnetic field effect due to Δg mechanism).Neither an HFI nor a Δg magnetic field effect was observed in the presence of 1,3-pentadiene.The reaction was thus concluded to proceed from the S1 and T1 states via the singlet and triplet radical pairs.Reaction mechanisms deduced from the external magnetic field effects were consistent with the results of Stern-Volmer analyses.

Visible-light-mediated photoredox decarbonylative Minisci-type alkylation with aldehydes under ambient air conditions

Visible-light-induced photoredox decarbonylative C-C bond formation with aldehydes is described for the first time. Minisci-type alkylation reactions of N-heteroarenes proceed smoothly at ambient temperature with air as the sole oxidant. The present sustainable protocol uses readily available organofluorescein as a photocatalyst, cheap and green oxidant and a sustainable power source, thus featuring potential for applications in late-stage modification of valuable molecules.

Substituted 4-methylquinolines as a new class of anti-tuberculosis agents

We report synthesis and anti-tuberculosis activities of a series of novel ring-substituted quinolines. The most effective compound of the series 3d (MIC=6.25 μg/mL, Mycobacterium tuberculosis H37Rv strain) was synthesized in one step; thus is an attractive lead molecule for anti-tuberculosis drug development. The results of this study represent the discovery of ring-substituted 4-methylquinolines as new class of potential anti-tuberculosis agents.

Minisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light

A synthetic method that enables the Hantzsch ester-mediated Minisci-type C2-alkylation of quinolines, isoquinolines and pyridines by N-(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal-free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N-heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron-donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N-heterocycle.

Synthesis method of alkylated quinoline compound

The invention relates to a synthesis method of an alkylated quinoline compound. According to the method, under the irradiation of an ultraviolet LED lamp, in the presence of a catalyst, an acid additive and a solvent, the alkylated quinoline and the deriv

Direct functionalization of quinoxalin-2(1H)-one with alkanes: C(sp2)-H/C(sp3)-H cross coupling in transition metal-free mode

Considering the significance of pharmaceutically important heterocycles, efficient and highly versatile protocols for the functionalization of diverse heterocycles with easily accessible feedstock are crucial. Here, we have reported selective alkylation of quinoxalin-2(1H)-one with a broad class of hydrocarbons having different C(sp3)-H bonds with varying bond strengths using di-tert-butyl peroxide (DTBP) as an alkoxyl radical mediator for hydrogen atom transfer (HAT). This dehydrogenative coupling approach utilizes feedstock chemicals such as cycloalkanes, cyclic ethers and alkyl arenes as coupling partners. This protocol exhibits good functional group compatibility and selectivity regarding both heterocycles and unactivated alkanes. Moreover, this methodology allows functionalization of relatively strong C-H bonds of adamantane and exclusive selectivity towards 3° C(sp3)-H bonds is observed. We also illustrate the applicability of this C(sp2)-H/C(sp3)-H cross-coupling for practical access to bioactive pharmaceuticals.

Time-Resolved EPR Revealed the Formation, Structure, and Reactivity of N -Centered Radicals in an Electrochemical C(sp3)-H Arylation Reaction

Electrochemical synthesis has been rapidly developed over the past few years, while a vast majority of the reactions proceed through a radical pathway. Understanding the properties of radical intermediates is crucial in the mechanistic study of electroche

Alkylation method of nitrogen-containing heterocyclic compound

The invention discloses an alkylation method of a nitrogen-containing heterocyclic compound. The method is characterized by comprising the following steps: mixing the nitrogen-containing heterocyclic compound, an alkyl reagent, an acid, peroxide, a Select