Benzimidazole N-Oxides. VIII. The Reactivity of Ethyl 1-Methyl-2-benzimidazolecarboxylate 3-Oxide and the Related Compounds
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概要
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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.
- 公益社団法人日本薬学会の論文
- 1968-03-25
著者
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高橋 史郎
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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加納 日出夫
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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高橋 史郎
Shionogi Research Laboratory Shionogi & Co. Ltd.
-
加納 日出夫
Shionogi Research Laboratory Shionogi & Co. Ltd.
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