Synthesis and reactions of 2-arylhydrazinotropones. II. Synthesis of 5-aryltropolones and B-ring-open colchicine analogues via benzidine type rearrangement of 2-(2-arylhydrazino)tropones.

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概要

• 論文の詳細を見る

• Treatment of a wide variety of 2-(2-arylhydrazino)tropones with ethanolic acid at 50–80°C readily gave the benzidine type rearrangement products, 2-amino-5-(4-aminoaryl)tropones, besides minor amounts of byproducts of various type. The main products were conveniently led to the corresponding 5-aryltropolones. Similarly, 2-(2-arylhydrazino)tropones bearing an isopropyl and isopropenyl group at the 4-position afforded 4-substituted 2-amino-5-(4-aminoaryl)tropones as the main products, which were also led to 4-substituted 5-(4-acetamidoaryl)- and 5-(4-methoxyaryl)tropolones. Structural assignments of these products were made on the basis of <SUP>1</SUP>H NMR and other spectral data as well as of chemical transformations to known 5-phenyltropolone and also to 2-acetamido-8-hydroxy-10,10-dimethylcyclohept[<I>a</I>]inden-7(10<I>H</I>)-one. This synthetic scheme may possibly be utilized for a convenient synthesis of B-ring-open analogues of colchicine.

• 公益社団法人 日本化学会の論文

著者

• Nozoe Tetsuo

  Tokyo Research Laboratories Kao Corporation

• Ando Masayoshi

  Department of Applied Chemistry, Niigata University

• Hara Yasushi

  Department Of Anatomy And Neurosurgery Shiga University Of Medical Science

• Yasunami Masafumi

  Department Of Chemistry Faculty Of Science Tohoku University

• Hanaya Tadashi

  Department Of Chemistry Faculty Of Science Okayama University

• Honda Masaaki

  Department Of Computer Engineering Waseda University

• IMAFUKU Kimiaki

  Department of Chemistry, Faculty of Science, Kumamoto University

• Takase Kahei

  Department Of Chemistry Faculty Of Science Tohoku University

• Saito Hiroaki

  Department Of Applied Chemistry Graduate School Of Engineering Tohoku University

• Yamamoto Hiroshi

  Departmemt Of Chemical Engineering University Of Tokyo

• Yin Bing-Zhu

  Department of Chemistry, Faculty of Science, Kumamoto University

• Goto Yasutomo

  Department of Chemistry, Faculty of Science, Kumamoto University

• Nozoe Tetsuo

  Tokyo Reseach Laboratory of Kao Soap Co., Ltd.

• Honda Masaaki

  Department of Chemistry, Faculty of Science, Kumamoto University

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