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Development of Innovative Synthetic Method of Diazanaphthalene Rings from Hydrazine-Carbonyl Analogs and TCNE

Research Project

Project/Area Number 09650944
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionKinki University

Principal Investigator

MATSUBARA Yoshio  Faculty of Science and Engineering, Kinki University Professor, 理工学部, 教授 (80088450)

Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 1998: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1997: ¥1,700,000 (Direct Cost: ¥1,700,000)
KeywordsDiazanaphthalenes / Ring formation reaction / New synthetic reaction / Phenylhydrazines / Carbonyl compounds / TCNE / Three components reaction system / カルボニル類
Research Abstract

Innovative new synthetic reaction of diazanaphthalenes which are important as key compounds for medicines and functional materials, were found by the reaction of three components system of phenyihydrazines, carbonyls and TONE.
The results were noticeable such as showing below.
1)Synthesis of diazanaphthalenes was investigated by the various reaction conditions such as reaction media, solvents and reaction temperature. The results were obtained the establishment of new synthetic method and the elucidation for the range of application by substitution and functional group.
2)Based on the finding results from the 1 was variously investigated.The results clearly suggest that the reaction proceed initially by the initiation with a charge transfer, via formation of additional intermediate between hydrazone and TONE (1 : 1), elimination of methyl group and finally ring formation by ON of TCNE.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] Y.Matsubara, T.Matsuda, Y.Yamaguchi, Z.Yoshida: "Remarkably Different Behavior of 4-Cyano-3-phenylcinnoline Toward Chemical and Electrochemical Reductions" Tetrahedron Lett.,. in press.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Matsubara, A.Horikawa Z.Yoshida,: "A Novel Synthesis of 1, 2-Diazanaphthalenes" Tetrahedron Lett.,. 38. 8199-8202 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Matsubara, T.Matsuda, Y.Yamaguchi, Z.Yoshida: "Remarkably Different Behavior of 4-Cyano-3-phenylcinnoline Toward Chemical and Electrochemical Reductions" Tetrahedron Lett.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Matsubara, A.Horikawa, Z.Yoshida: "A Novel Synthesis of 1,2-Diazanaphthalenes" Tetrahedron Lett.38 (47, Nov). 8199-8202 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 松原凱男: "Synthesis of Novel 2-Substituted-1,3,4-thiadiazoles." Chem.Pharm.Bull.46. 392-331 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 松原凱男: "Remarkably Different Behavior of 4-Cyano-3-phenylcinnoline Toward Chemical and Electrochemical Reductions" Tetrahedron Lett.(in press).

    • Related Report
      1998 Annual Research Report
  • [Publications] 松原凱男: "Reaction of Aromatic Hydrazones with Tetracyanoethylene Leading to the Formation of Cyanocinnoline" (発表予定).

    • Related Report
      1998 Annual Research Report
  • [Publications] 松原凱男: "Echochemicaly Ideal Reaction producting a New Class of Merocyanines" (発表予定).

    • Related Report
      1998 Annual Research Report
  • [Publications] 松原凱男、吉田善一: "A Novel Synthesis of 1,2-Diazanaphthalenes" Tetrahedron Lett.38. 8199-8202 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 松原凱男: "Synthesis of Novel 2-Substituted-1,3,4-thiadiazoles" Chem.Pharm.Bull.46. 331-392 (1998)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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