Studies on Heteroaromatic N-Oxides. XI. Aminolysis of Esters of Benzazole N-Oxides and Related Quaternary Salts

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公開日
1973
DOI
  • 10.1248/cpb.21.287
公開者
公益社団法人 日本薬学会

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説明

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-methoxycarbonylmethyl- 1, 3-dimethylbenzimidazolium iodide (17), ethyl 2-benzothiazolecarboxylate 3-oxide (26) and 2-ethoxycarbonyl-3-methylbenzothiazolium 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.<BR>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 both primary and secondary amines to yield only normal products, amides.<BR>Mechanisms accounting for the different behavior of the esters towards amines have been discussed from electronic and steric points of view.

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