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化学学报
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化学学报 ›› 1962, Vol. 28 ›› Issue (2): 108-113. 上一篇    下一篇

论文

几种硝基-甲基(或烷氧基)-吲(口乃木)-2-羧酸乙酯及其相应氨基化合物的合成

翁尊尧1, 王崇言2, 王鼎3   

  1. 1. 中国科学院药物研究所;
    2. 上海第一医学院化学教研组;
    3. 天津市卫生局药物研究所
  • 投稿日期:1961-09-13 发布日期:2013-06-03

SYNTHESIS OF SEVERAL ETHYL NITRO-METHYL(OR ALKOXY)-INDOLE-2-CARBOXYLATES AND THEIR CORRESPONDING AMINO COMPOUNDS

OWEN TSUNG-YAO1, WANG CHUNG-YEN2, WANG TINC3   

  1. Institute of Materia Media, Academia Sinica
  • Received:1961-09-13 Published:2013-06-03

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1.从硝基苯胺及其取代物经三步反应合成六种氨基-甲基(或烷氧基)-吲(口朶)-2-羧酸乙酯(Ⅱ)。2.两种氨基-甲基-吲(口朶)-2-羧酸乙酯(Ⅱb和Ⅱc)经羟乙基化后得5-[双-(β-羟乙基)-氨基]-3-甲基-吲(口朶)-2-羧酸乙酯(Ⅵa)和4-[双-(β-羟乙基)-氨基]-7-甲基-吲(口朶)-2-羧酸乙酯(Ⅵb)。3.由硝基-吲(口朶)-2-羧酸酯(Ⅻa及Ⅻb)经脱羧及催化氢化制得5-氨基-吲(口朶)(Ⅸa)和7-氨基-吲(口朶)(Ⅸb)。

A series of ethyl vitro-methyl-(or alkoxy)-indole-2-carboxylates (Ⅵ) and their corresponding amino compounds (Ⅱ) was prepared. Nitroanilines (Ⅲ) were converted to their diazonium salts. The diazonium salts condensed with ethyl alkylacetoacetate in presence of potassium hydroxide, to give the vitro-phenylhydrazones of ethyl-ketoesters (Ⅳ). Compounds (Ⅳ) were then cyclized with the aid of polyphosphoric acid to substituted vitro indole-2-carboxylates (Ⅴ) and the latter were subsequently reduced to the final products (Ⅱ).