108771-06-8

Upstream product

• 4363-93-3 quinoline-4-carboxaldehyde 
• 98-80-6 phenylboronic acid 
• 91-22-5 quinoline 
• 5632-14-4 4-benzylquinoline 
• 100-52-7 benzaldehyde 
• 3964-04-3 4-bromoquinoline 
• 108770-98-5 4-(Toluene-4-sulfinyl)-quinoline 

Relevant academic research and scientific papers

Synthesis and reactivity of lithium tri(quinolinyl)magnesates

2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolinyl)magnesates at -10°C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.

Green synthesis method of polyaryl substituted methanol

The invention relates to a green synthesis method of polyaryl substituted methanol, in particular to a method for efficiently synthesizing polyaryl substituted methanol in a polar aprotic solvent under the condition of an oxidizing agent by taking polyaryl substituted methane as a raw material and alkali as an additive. The method provided by the invention is green and environment-friendly, avoids using expensive metal catalysts, and has the advantages of low cost, few reaction steps, short time, high yield and the like.

Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes

We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

Photochemical C?H Hydroxyalkylation of Quinolines and Isoquinolines

We report herein a visible light-mediated C?H hydroxyalkylation of quinolines and isoquinolines that proceeds via a radical path. The process exploits the excited-state reactivity of 4-acyl-1,4-dihydropyridines, which can readily generate acyl radicals upon blue light absorption. By avoiding the need for external oxidants, this radical-generating strategy enables a departure from the classical, oxidative Minisci-type pattern and unlocks a unique reactivity, leading to hydroxyalkylated heteroarenes. Mechanistic investigations provide evidence that a radical-mediated spin-center shift is the key step of the process. The method's mild reaction conditions and high functional group tolerance accounted for the late-stage functionalization of active pharmaceutical ingredients and natural products.

Efficient 1,2-addition of aryl- and alkenylboronic acids to aldehydes catalyzed by the palladium/thioether-imidazolinium chloride system

(Chemical Equation Presented) The high level of catalyst performance was attainable in the palladium-catalyzed 1,2-addition of aryl-, heteroaryl-, and alkenylboronic acids to aromatic, heteroaromatic, and aliphatic aldehydes using thioether-imidazolinium chloride L5 as a heterobidentate carbene ligand precursor.

Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether-imidazolinium carbene ligands

(Chemical Equation Presented) Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether- imidazolinium carbene ligands proceeded readily under aqueous conditions. This process tolerated a diverse range of potassium trifluoroborate salts and aldehydes, giving a variety of carbinol derivatives with good to excellent yields.

Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines: A convenient access to functionalized quinolines

2-, 3- and 4-bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C by treatment with Bu3MgLi in THF or toluene. The resulting organomagnesium derivatives were quenched by various electrophiles to afford functionalized quinolines.

4-Quinolinemethanol derivatives as purine receptor antagonists (1)

Use a compound of formula (I) wherein: R1is hydrogen or alkyl; R2and R3are independently selected from hydrogen, alkyl, aryl and heterocyclyle or together may form a ring or R1and R2or R3together may form an oxygen-containing, optionally fused ring pharmaceutically acceptable salts or prodrugs thereof, with the proviso that where R1and R4to R9are hydrogen, R2or R3is not 3-methoxy-4-benzyloxyphenyl or 2-dimethylaminoethoxymethyl, in the manufacture of a medicament for the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A2Areceptors, may be beneficial. Said disorders are neurodegenerative disorders or movement disorders selected from Parkinson's disease or progressive supernuclear palsy, Huntington's disease, multiple system atrophy, corticobasal degeneration, Wilson's disease, Hallerrorden-Spatz disease, progressive pallidal atrophy, Dopa-responsive dystonia-Parkinsonism, spasticity, Alzheimer's disease or other disorders of the basal ganglia which result in dyskinesias.

REACTIONS OF PYRIDYL AND QUINOLYL SULFOXIDES WITH GRIGNARD REAGENT : A CONVENIENT PREPARATION OF PYRIDYL AND QUINOLYL GRIGNARD REAGENTS

3-,4-Pyridyl and 4-quinolyl Grignard reagents were generated by the reaction of the corresponding phenyl sulfoxides with PhMgBr and give the adducts upon treatment with various aldehydes and ketones.The stereochemistry for the reaction was investigated.