Studies on Heteroaromatic N-Oxides. XI. Aminolysis of Esters of Benzazole N-Oxides and Related Quaternary Salts
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概要
- 論文の詳細を見る
In connection with the abnormal reaction of ethyl 1-methyl-2-benzimidazolecarboxylate 3-oxide (1) with piperidine, aminolyses of several related esters were investigated. The esters : 1,2-ethoxycarbonyl-1,3-dimethylbenzimidazolium iodide (11), 2-methoxy-carbonylmethyl-1,3-dimethylbenzimidazolium iodide (17), ethyl 2-benzothiazolecarboxylate 3-oxide (26) and 2-ethoxycarbonyl-3-methylbenzothiazothiazolium perchlorate (34) under went abnormal aminolysis partly or predominantly, not only with secondary amine (piperidine) but also with some primary amines, to give the corresponding carbamates. Ethyl tribromoacetate (57) also underwent abnormal cleavage with some primary amines. On the other hand, ethyl 1-methyl-2-benzimidazolecarboxylate (21), ethyl 2-benzothiazolecarboxylate (37), ethyl 2-and 4-pyridinecarboxylate N-oxide (44,45) 4-ethoxycarbonyl-1-methylpyridinium iodide (55) reacted with primary and secondary amines to yield only normal products, amides. Mechanisms accounting for the different behavior of the esters towards amines have been discussed from electronic and steric points of view.
- 公益社団法人日本薬学会の論文
- 1973-02-25
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.
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橋本 進一郎
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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橋本 進一郎
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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