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Synthetic Studies on the Biologically Active 3-Benzazepines

Research Project

Project/Area Number 63571013
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKyoto Pharmaceutical University

Principal Investigator

IKEDA Masazumi  Kyoto Pharm. Univ., Professor, 薬学部, 教授 (30028857)

Co-Investigator(Kenkyū-buntansha) ISHIBASHI Hiroyuki  Kyoto Pharm. Univ., Associate Professor, 薬学部, 助教授 (70028869)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1989: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1988: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywords2-Phenethylamine / 3-Benzazepine / 3-Benzazepin-2-one / Sulfoxide / Pummerer reaction / X-Ray analysis / Cephalotaxine / 2-フェネチルアミン / 3-ベンズアゼピン / 3-ベンズアゼピン-2-オン / X-線結晶解析
Research Abstract

1. A series of (methylsulfinyl)acetamides reacted with electron-rich arenes in the presence of p-toluenesulfonic acid to give alpha-(methylthio)aryl- acetamides, some of which were transformed into biologically active aryl- ethylamines such as (<plus-minus>)-macromerin
2.1,3,4,5-Tetrahydro-2H-3-benzazepin-2-one derivatives were synthesized by an acid-catalyzed cyclization of N-(2-arylethyl)-N-methyl-2-sulfinylacet- amides. Some chemical transformations of the 2H-3-benzazepin-2-ones were also investigated.
3. Synthesis of 1,3,5,6,9,15-hexahydro-4H-1,3-dioxolo[4,5-h]pyrrolo[2,1-b]- [3]benzazepin-2(1H),8-dione, a key intermediate for the total synthesis of (<plus-minus>)-cephalotaxine, has been achieved in a stereoselective manner by a synthetic sequence involving an acid-catalyzed cylization of the alpha- sulfinylacetamide as a key ste

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (15 results)

All Other

All Publications (15 results)

  • [Publications] 石橋弘行: "A Convenient Synthesis of 1,3,4,5-Tetrahydro-2H-3-benz-azepin-2-ones by Acid-Catalyzed Cyclization of N-(2-Arylethyl)-N-methyl-2-sulfinylacetamides" Chem.Pharm.Bull.37. 939-943 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 石橋弘行: "A New,Convenient Route to Erbstatin and N-Acetyl-1,2-didehydrodopamine" Chem.Pharm.Bull.37. 2214-2216 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 石橋弘行: "Synthesis of-(Methylthio)arylacetamides and Their Conversion into Some Biologically Active Arylethylamines" Chem.Pharm.Bull.37. 3396-3398 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 石橋弘行: "A Formal Total Synthesis of (±)-Cephalotaxine" J.Chem.Soc.Chem.Commun.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 石橋弘行: "「薬学研究の進歩」研究成果報告集5" 薬学奨励財団, 13 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hiroyuki Ishibashi: "A Convenient Synthesis of 1, 3, 4, 5-Tetrahydro-2H-3-benzazepin-2-ones by Acid-Catalyzed Cyclization of N-(2-Arylethyl)-N-methyl-2-sulfinylacetamides" Chem. Pharm. Bull., 37, 939-943 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hiroyuki Ishibashi: "A New, Convenient Route to Erbstatin and N-Acetyl-1, 2-didehydrodopamine" Chem Pharm. Bull., 37, 2214-2216 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] "Synthesis of alpha-(Methylthio)arylacetamides and Their Conversion into Some Biologically Active Arylethylamines" Chem. Pharm. Bull., 37, 3396-3398 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hiroyuki Ishibashi: "A Formal Total Synthesis of (<plus-minus>)-Cephalo-taxi " J. Chem. Soc., Chem. Commun.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 石橋弘行: "A Convenient Synthesis of 1,3,4,5-Tetrahydro-2H-3-benz-azepin-2-ones by Acid-Catalyzed Cyclization of N-(2-Arylethy1)-N-methy1-2-sulfinylacetamides" Chem.Pharm.Bull.37. 939-943 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 石橋弘行: "A New,Convenient Route to Erbstatin and N-Acetyl-1,2-didehydrodopamine" Chem.Pharm.Bull.37. 2214-2216 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 石橋弘行: "Synthesis of-(Methylthio)arylacetamides and Their Conversion into Some Biologically Active Arylethylamines" Chem.Pharm.Bull.37. 3396-3398 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 石橋弘行: "A Formal Total Synthesis of(±)-Cephalotaxine" J.Chem.Soc.Chem.Commun.

    • Related Report
      1989 Annual Research Report
  • [Publications] 石橋弘行: "「薬学研究の進歩」研究成果報告集5" 薬学奨励財団, 13 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 石橋弘行: Chem.Pharm.Bull.

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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