6829-11-4

Upstream product

• 108-86-1 bromobenzene 
• 53153-95-0 α,β-dimethyl-β-phenylpropionitrile 
• 67-56-1 methanol 
• 5278-43-3 3-methyl-2-phenyl-quinoline 
• 551-93-9 2-aminoacetophenone 
• 673-32-5 1-Phenylprop-1-yne 
• 146954-11-2 1-(2-azidophenyl)ethan-1-ol 
• 941706-81-6 1-(2-aminophenyl)ethanol 
• 100-52-7 benzaldehyde 
• 4393-06-0 1-Phenyl-2-propen-1-ol 

Relevant academic research and scientific papers

Preparation of 2-arylquinolines from β-arylpropionitriles with aryllithiums and NIS through iminyl radical-mediated cyclization

Treatment of β-arylpropionitriles with aryllithiums, followed by the reaction with water and then with NIS under irradiation with a tungsten lamp gave 2-arylquinolines in good to moderate yields. The present reaction proceeds through the formation of N-iodoimines from imines with NIS, the generation of imino-nitrogen-centered radicals, and their cyclization onto the aromatic rings of the imines to form 2-aryl-3,4-dihydroquinolines. Finally, the oxidation of 2-aryl-3,4-dihydroquinolines with NIS proceeds smoothly to generate 2-arylquinolines.

Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH

Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both the solvent and the methylation source. It was found that adding dichloromethane (DCM) as a co-solvent could significantly increase the yield of the methylation products. Heteroarenes bearing various functional groups could be methylated and tri-deuteromethylated successfully. Deuterium labeling studies suggested that the newly generated methyl group in the products consisted of two hydrogens from the methyl group and one hydrogen from the OH group in MeOH.

Metal free carboamination of internal alkynes - An easy access to polysubstituted quinolines

A metal free carboamination of unactivated alkynes towards highly substituted quinolines was realized in the presence of a synergistic Br?nsted acid catalyst system. Supported by mechanistic probes, the reaction proceeds via a highly reactive vinyl cation in a C-C bond formation - Schmidt reaction sequence. The irreversible extrusion of N2, as a powerful driving force, allows for a general conversion of poorly nucleophilic aliphatic alkynes.

Synthesis of Quinolines from Allylic Alcohols via Iridium-Catalyzed Tandem Isomerization/Cyclization Combined with Potassium Hydroxide

A new tandem catalytic process has been established for the synthesis of quinolines. This process utilizes the [IrCp?Cl2]2/KOH catalyzed isomerization/cyclization of allylic alcohols with 2-aminobenzyl alcohol. Both the secondary and primary allylic alcohols were investigated in this catalytic system to afford different substituted quinoline derivatives in moderate to good yields. A mechanism study showed the reaction following a tandem process integrating isomerization of allylic alcohols and oxidative cyclization of 2-aminobenzyl alcohol.