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Practical synthetic reactions using functionalized trimethylsilyldiazomethanes

Research Project

Project/Area Number 21790021
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionOsaka University

Principal Investigator

HARI Yoshiyuki  Osaka University, 大学院・薬学研究科, 特任准教授 (50347423)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywords有機合成化学 / 複素環合成 / トリメチルシリルジアゾメタン / ベンズアゼピン / インダゾール / ベンゾフラン / アシルシラン
Research Abstract

Application of functionalized trimethylsilyldiazomethanes to organic reactions was investigated in this work. It was found that an intermolecular [3+2]cycloaddition between functionalized trimethylsilyldiazomethanes and benzynes, in situ generated from (o-trimethylsilyl)aryl trifluoromethanesulfonates, efficiently afforded the corresponding 3-substituted indazoles. In addition, it was achieved that the synthesis of highly functionalized acylsilanes by oxidation of functionalized trimethylsilyldiazomethanes and the synthesis of 1-methyl-1-benzazepines from 1-methylquinolinium salts via ring expansion reactions. A new synthetic method of benzofurans from o-anisyl(oxo)acetates and diazo(trimethylsilyl)methylmagnesium bromide, a precursor for the preparation of functionalized trimethylsilyldiazomethanes, was also found.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (10 results)

All 2010 2009

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (4 results)

  • [Journal Article] Facile synthesis of 1-methyl-1H-benzo[b]azepines from 1-methylquinolinium iodides and diazo(trimethylsilyl)methylmagnesium bromide2010

    • Author(s)
      M.Morita, Y.Hari, T.Aoyama
    • Journal Title

      Synthesis

      Pages: 4221-4227

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of 1-methyl-1 H-benzo[b]azepines from 1-methylquinolinium iodides and diazo(trimethylsilyl)methylmagnesium bromide2010

    • Author(s)
      M.Morita, Y.Hari, T.Aoyama
    • Journal Title

      Synthesis

      Pages: 4221-4227

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of 2-unsubstituted benzofuran-3-carboxylates using diazo(trimethylsilyl)methylmagnesium bromide2009

    • Author(s)
      Y.Hari, R.Kondo, K.Date, T.Aoyama
    • Journal Title

      Tetrahedron 65

      Pages: 8708-8713

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile two-step synthesis of 3-substituted indazoles using diazo(trimethylsilyl)methylmagnesium bromide2009

    • Author(s)
      Y.Hari, R.Sone, T.Aoyama
    • Journal Title

      Org.Biomol.Chem. 7

      Pages: 2804-2808

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile two-step synthesis of 3-substituted indazoles using diazo (trimethylsilyl) methylmagnesium bromide2009

    • Author(s)
      Y.Hari, R.Sone, T.Aoyama
    • Journal Title

      Org.Biomol.Chem. Vol.7

      Pages: 2804-2808

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of 2-unsubstituted benzofuran-3-carboxylates using diazo (trimethylsilyl) methylmagnesium bromide2009

    • Author(s)
      Y.Hari, R.Kondo, K.Date, T.Aoyama
    • Journal Title

      Tetrahedron Vol.65

      Pages: 8708-8713

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] トリメチルシリルジアゾメタンのMgBr塩を用いたα-ヒドロキシアシルシランの合成2009

    • Author(s)
      曽根良介, 張功幸, 青山豊彦
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2009-11-07
    • Related Report
      2010 Final Research Report
  • [Presentation] トリメチルシリルジアゾメタンのMgBr塩を用いたα-ヒドロキシアシルシランの合成2009

    • Author(s)
      曽根良介, 張功幸, 青山豊彦
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢市文化ホール(金沢)
    • Year and Date
      2009-11-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] indazoles using [3+2]cycloaddition reactions of 2-diazo-2-(trimethylsilyl)ethanols2009

    • Author(s)
      Y.Hari, R.Sone, T.Aoyama
    • Organizer
      22^<nd> International Congress on Heterocyclic Chemistry
    • Place of Presentation
      St John's, Canada
    • Year and Date
      2009-08-03
    • Related Report
      2010 Final Research Report
  • [Presentation] Facile synthesis of 3-substituted pyrazoles and indazoles using [3+2] cycloaddition reactions of 2-diazo-2- (trimethylsilyl) ethanols2009

    • Author(s)
      Y.Hari, R.Sone, T.Aoyama
    • Organizer
      22_<nd> International Congress on Heterocyclic Chemistry
    • Place of Presentation
      The Delta Hotel (St John's, Canada)
    • Year and Date
      2009-08-03
    • Related Report
      2009 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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