Shirō Takahashi, H. Kanō
Mar 25, 1968
Citations
0
Influential Citations
17
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
Ethyl 1-methyl-2-benzimidazolecarboxylate 3-oxide (XVII) was synthesized from 1-methyl-2-benzimidazolecarboxaldehyde oxime 3-oxide via the corresponding nitrile (III) and imido ester (XIII). Both reactions of III and XIII with potassium hydroxide gave 1-methyl-2-benzimidazolol 3-oxide. From III, 2-carboxamide (XI), 2-thiocarboxamide derivatives and 6-hydroxy-1-methyl-2-benzimidazolecarbonitrile were obtained. L-2-(6-Hydroxy-1-methyl-2-benzimidazolyl)-△2-thiazoline-4-carboxylic acid was synthesized from III, which has an analogous structure to firefly luciferin but it was inactive as far as light production was concerned. From XIII, 2-amidrazone, 2-tetrazole derivative and 1, 1'-dimethyl-2, 2'-bibenzimidazole 3-oxide were prepared. Hydrolysis of III and XIII with hydrochloric acid gave 1-methylbenzimidazole 3-oxide. The corresponding amide XI, acid hydrazide and hydroxamic acid were obtained from XVII. Reaction of XVII with piperidine did not give the corresponding amide but a mixture of 1-methylbenzimidazole 3-oxide and piperidine urethan. 3-(α, β-Dimethoxycarbonyl-β-hydroxyvinyl)-2-ethoxycarbonyl-1-methylbenzimidazolium betaine was prepared from XVII and dimethyl acetylenedicarboxylate.