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

Article abstract of DOI:10.3987/COM-96-S40

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).