ニトロフラン誘導体の研究(第9報)5-Nitro-2-furoyl Isothiocyanateおよび5-Nitro-2-thiofuroyl Isocyanateとβ-アミノクロトン酸エステル類との反応

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概要

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• Reaction of 5-nitro-2-furoyl isothiocyanate (1) and 5-nitro-2-thiofuroyl isocyanate (2), having a strong electron-withdrawing group, with β-aminocrotonates (3a-d) was examined. The products from the reaction of 1 with 3a-d were proved to be isothiazoles (5a-d) from chemica1 and spectral evidences. And of the expected compounds such as 1,2- and 1,4-adducts (4 and 6) and pyrimidines (7) were not obtained by these reactions. The isothiazoles were probably formed from 1,2-addition of 3 to 1 giving 1 : 1 adducts (4), followed by cyclization with loss of hydrogen. In order to examine the role of the nitro group in this reaction, p-nitrobenzoyl and 2-furoyl isothiocyanate (10a and 10b) were treated with 3b under the same conditions, resulting in the formation of pyrimidines (11a and 11b) ; the corresponding isothiazoles (12a and 12b) were obtained in the presence of bromine as an oxidizing agent. Formation of isothiazoles (5a-d) from 1,without oxidizing agents appeared to be specific for nitrofuran derivatives. On the other hand, the products from the reaction of 2 with 3a-c were found to be linear 1;2-adducts (14a-c) from spectral evidinces.

• 公益社団法人日本薬学会の論文
• 1975-11-25

著者

• 松本 純一

  Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.

• 松本 純一

  大日本製薬株式会社 総合研究所

• 松本 純一

  Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• 三塩 晋作

  大日本製薬株式会社 総合研究所

• 南 新作

  大日本製薬株式会社 総合研究所(現)

• 松本 純一

  大日本製薬 総研

• 南 新作

  大日本製薬株式会社 総合研究所(現):帝国化学産業株式会社研究所

• 南 新作

  大日本製薬株式会社

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