187875-25-8

Upstream product

• 1632-83-3 1-Methylbenzimidazole 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 55276-54-5 quinazolin-4-yl-p-tolyl-methanone 
• 99934-05-1 (3-Phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-p-tolyl-methanone 
• 1218-89-9 4,4'-dimethylbenzoin 
• 59563-95-0 (1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-p-tolyl-methanone 

Relevant academic research and scientific papers

Formation of deoxybenzoins from 1,3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides through rearrangement followed by expulsion of azolium ylide

Treatment of several 1,3-dimethyl-2-(α-benzyloxybenzyl)benzimidazolium iodides 1 with K2CO3 gave deoxybenzoins 2 in moderate yields. Deoxybenzoins 2 were produced through rearrangement of benzyl groups followed by expulsion of 1,3-dimethylbenzimidazolium ylide (4). The reaction is classified as a Wittig rearrangement.

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).