Fischer Indolization and Its Related Compounds. XXIV. Fischer Indolization of Ethyl Pyruvate 2-(2-Methoxyphenyl)phenylhydrazone

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概要

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• In order to clarify the mechanism of Fischer indolization of 2-methoxyphenylhydrazones, Fischer indolization of ethyl pyruvate 2-(2-methoxyphenyl)phenylhydrazone (2) was carried out with hydrochloric acid in ethanol and zinc chloride in acetic acid. The reactions proceeded smoothly to give N-arylindoles (11-14) and some chlorinated diphenylamine derivatives (8-10) as by-products. Consideration of the indole products revealed that the Fischer indolization proceeded mainly at the unsubstitued phenyl nucleus rather than at the 2-methoxyphenyl nucleus. This result is inconsistent with the previous result that Fischer indolization of diarylhydrazones proceeded at the electron-richer nucleus. The structures of the diphenylamines were determined by chemical means and the mechanism of their formation is discussed.

• 公益社団法人日本薬学会の論文
• 1991-03-25

著者

• 石井 永

  Faculty of Pharmaceutical Sciences, Chiba University

• 渡辺 敏子

  千葉大院薬

• 渡辺 敏子

  School Of Pharmaceutical Sciences Toho University

• 石井 永

  Faculty Of Pharmaceutical Sciences Chiba University

• 村上 泰興

  School of Pharmaceutical Sciences, Toho University

• Murakami Yukihisa

  富山大学和漢医薬学総合研究所 複合薬物薬理学

• Mukarami Yukihisa

  Institute Of Natural Medicine Toyama Medical And Pharmaceutical University

• Murakami Yukihisa

  Division Of Medicinal Pharmacology Institute Of Natural Medicine Toyama Medical And Pharmaceutical U

• Murakami Yukihisa

  Research Institute For Wakan-yaku (traditional Sino-japanese Medicines)

• 杉浦 孝夫

  Faculty Of Pharmaceutical Sciences Chiba University

• Watanabe Toshifumi

  Pharmaceutical Research Laboratories Ii Pharmaceutical Research Division Takeda Chemical Industries

• Watanabe T

  Chiba Univ. Chiba Jpn

• 小薬 公子

  Faculty of Pharmaceutical Sciences, Chiba University

• Watanabe Toshiko

  Faculty Of Pharmaceutical Sciences Chiba University

• Watanabe Toshihiro

  Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.

• 小薬 公子

  Faculty Of Pharmaceutical Sciences Chiba University

• Murakami Y

  Department Of Bioactive Molecules National Institute Of Infectious Diseases

• Ishii H

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• 村上 泰興

  School Of Pharmaceutical Science Toho University

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