122155-24-2

Upstream product

• 30148-18-6 4-chlorophenyl 1-methylimidazol-2-yl ketone 
• 616-47-7 1-methyl-1H-imidazole 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 1613633-19-4 2-((4-chlorophenyl)((4-fluorobenzyl)oxy)methyl)-1-methyl-1H-imidazole 
• 502552-76-3 4-fluorobenzyl 4-chlorobenzoate 
• 1613633-20-7 3-butyl-2-((4-chlorophenyl)((4-fluorobenzyl)oxy)methyl)-1-methyl-1H-imidazol-3-ium iodide 
• 59563-90-5 (4-chloro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 55276-59-0 (4-chloro-phenyl)-quinazolin-4-yl-methanone 

Relevant academic research and scientific papers

Asymmetric Transfer Hydrogenation of Aryl Heteroaryl Ketones using Noyori-Ikariya Catalysts

A range of ketones flanked by a combination of an aromatic and a heterocyclic ring (furan, thiophene, N-methylimidazole) were reduced under asymmetric transfer hydrogenation (ATH) conditions. Using a range of [(arene)Ru(TsDPEN)Cl] precatalysts, including tethered derivatives, the reduction enantioselectivity was high (up to 99 % ee) in cases where the aromatic ring contained an ortho-substituent. The enantioselectivity is influenced by a combination of steric and electronic factors which for the furan and thiophene series, follow literature precedents. In the case of the N-methylimidazole-containing ketones, an unexpected switch in enantioselectivity took place upon variation of the opposing aromatic group. Pyrrole- containing ketones were resistant to reduction. This study demonstrates the asymmetric transfer hydrogenation (ATH) of a range of hindered heterocyclic ketones, in high conversion and ee, using Noyori-Ikariya catalysts.

Electrogenerated N-heterocyclic carbene in ionic liquid: An insight into the mechanism of the oxidative esterification of aromatic aldehydes

An N-heterocyclic carbene (NHC), generated by cathodic reduction of BMIm BF4, mediates the oxidative esterification of aromatic aldehydes with organic bromides in the corresponding ionic liquid as solvent. The product recovery by simple extractive work-up with diethyl ether allowed the ionic liquid to be recycled up to 9 times for subsequent electrolyses, with no significant loss in the product yield. The isolation of an intermediate, whose structure was confirmed by synthesis and transformation into the ester, provided the key for a mechanistic insight into the reaction.

Synthesis and reactivities of 1,3-dimethyl-2-(α-hydroxy-benzyl)imidazolium and 1,3-dimethyl-2-(α-hydroxybenzyl)benzimidazolium iodides

1,3-Dimethyl-2-(α-hydroxybenzyl)benzimidazolium iodide (3a) was synthesized from 1-methylbenzimidazole (10) through two steps involving lithiation and quaternization. Treatment of 3a with 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (6) afforded 4-benzoyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (15a). 4-Benzoylquinazoline (14a) and 7-benzoyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (16a) were given by reaction of 3a with 4-chloroquinazoline (5) and 7-chloro-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (7). Treatment of 3a with benzaldehyde (9a) gave benzoin (8a). Similar results were obtained in the reactions of 1,3-dimethyl-2-(α-hydroxybenzyl)imidazolium iodide (4a).