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Development of hybrid domino reactions via multi-chemical species and the synthetic application

Research Project

Project/Area Number 20390008
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKobe Pharmaceutical University

Principal Investigator

NAITO Takeaki  Kobe Pharmaceutical University, 薬学部, 教授 (00068339)

Co-Investigator(Kenkyū-buntansha) MIYATA Okiko  神戸薬科大学, 薬学部, 教授 (90102110)
UEDA Masafumi  神戸薬科大学, 薬学部, 講師 (00340935)
MIYABE Hideto  兵庫医療大学, 薬学部, 教授 (10289035)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥19,240,000 (Direct Cost: ¥14,800,000、Indirect Cost: ¥4,440,000)
Fiscal Year 2010: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2009: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2008: ¥9,880,000 (Direct Cost: ¥7,600,000、Indirect Cost: ¥2,280,000)
Keywordsラジカル種 / イオン種 / ドミノ反応 / オキシムエーテル / 環境重視型反応 / ラジカル / イオン / テオン / カキシムエーテル
Research Abstract

Hybrid-type domino radical reactions of conjugated imine as a conjugated p-system were newly developed via the route involving various types of chemical species such as radical, ion, and organometallic species. Efficient synthetic methodology for highly functionalized products was developed via environmentally benign oxidation and radical-ionic domino reaction both of which proceeded via trapping the intermediates by atmospheric oxygen and appropriate electrophiles. Particularly, we were able to isolate unexpected reaction intermediates and thus succeeded in the development of powerful synthetic methods for various types of versatile and potential compounds by only one-manipulation.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (30 results)

All 2010 2009 2008 Other

All Journal Article (19 results) (of which Peer Reviewed: 9 results) Presentation (7 results) Remarks (4 results)

  • [Journal Article] Indium(I)-Mediated Radical Carbon-Carbon Bond-Forming Reaction in Aqueous Media2010

    • Author(s)
      Ueda Masafumi; Miyabe Hideto; Torii Masafumi; Kimura Takahiro; Miyata Okiko; Naito Takeaki
    • Journal Title

      Synlett

      Pages: 1341-1344

    • Related Report
      2010 Final Research Report
  • [Journal Article] Direct Synthesis of Trisubstituted Isoxazoles through Gold-Catalyzed Domino Reaction of Alkynyl Oxime Ethers2010

    • Author(s)
      Masafumi Ueda, Aoi Sato, Yuki Ikeda, Tetsuya Miyoshi, Takeaki Naito, Okiko Miyata
    • Journal Title

      Org.Lett. 12

      Pages: 2594-2597

    • Related Report
      2010 Final Research Report
  • [Journal Article] Synthesis of Fluorinated Imines by Addition of Fluoroalkyl Radicals to Conjugated Imines2010

    • Author(s)
      Ueda Masafumi, Iwasada Eri, Miyabe Hideto, Miyata Okiko, Naito Takeaki
    • Journal Title

      Synthesis

      Pages: 1999-2004

    • Related Report
      2010 Final Research Report
  • [Journal Article] Efficient Entry into 2-Substituted Tetrahydroquinoline Systems through Alkylative Ring Expansion : Stereoselective Formal Synthesis of (±)-Martinellic Acid2010

    • Author(s)
      Masafumi Ueda, Sayuri Kawai, Masataka Hayashi, Takeaki Naito, Okiko Miyata
    • Journal Title

      J.Org.Chem. 75

      Pages: 914-921

    • Related Report
      2010 Final Research Report
  • [Journal Article] Indium(I)-Mediated Radical Carbon-Carbon Bond-Forming Reaction in Aqueous Media2010

    • Author(s)
      上田昌史
    • Journal Title

      Synlett

      Volume: 9号 Pages: 1341-1344

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Synthesis of Trisubstituted Isoxazoles through Dold-Catalyzed Domino Reaction of Alkynyl Oxime Ethers2010

    • Author(s)
      上田昌史
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 2594-2597

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Fluorinated Imines by Addition of Fluoroalkyl Radicals to Conjugated Imines2010

    • Author(s)
      上田昌史
    • Journal Title

      Synthesis

      Volume: 12号 Pages: 1999-2004

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aerobic Hydroxylation of N-Borylenamine : Triethylborane-Mediated Hydroxyalkylation of α,β-Unsaturated Oxime Ether.2009

    • Author(s)
      Masafumi Ueda, Hideto Miyabe, Takahiro Kimura, Eiko Kondoh, Takeaki Naito, Okiko Miyata
    • Journal Title

      Org.Lett. 11

      Pages: 4632-4635

    • Related Report
      2010 Final Research Report
  • [Journal Article] Two Novel Domino Reactions Triggered by Thiyl-Radical Addition to Vinylcyclopropyl Oxime Ether.2009

    • Author(s)
      Habibur Rahaman, Masafumi Ueda, Okiko Miyata, Takeaki Naito
    • Journal Title

      Org.Lett. 11

      Pages: 2651-2654

    • Related Report
      2010 Final Research Report
  • [Journal Article] Carbon radical addition to N-sulfonylimines mediated by triethylborane or zinc.2009

    • Author(s)
      Masafumi Ueda, Hideto Miyabe, Okiko Miyata, Takeaki Naito
    • Journal Title

      Tetrahedron 65

      Pages: 1321-1326

    • Related Report
      2010 Final Research Report
  • [Journal Article] Aerobic Hydroxylation of N-Borylenamine : Triethylborane-Mediated Hydroxyalkylation of α, β-Unsaturated Oxime Ether2009

    • Author(s)
      上田昌史
    • Journal Title

      Org.Lett. 11

      Pages: 4632-4635

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two Novel Domino Reactions Triggered by Thiyl-Radical Addition to Vinylcyclopropyl Oxime Ether2009

    • Author(s)
      Habibur Rahaman
    • Journal Title

      Org.Lett. 11

      Pages: 2651-2654

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbon radical addition to N-sulfonylimines mediated by triethylborane or zinc2009

    • Author(s)
      上田昌史
    • Journal Title

      Tetrahedron 65

      Pages: 1321-1326

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Martinellic Acid via Radical Addition-Cyclization-Elimination Reaction.2008

    • Author(s)
      Atsushi Shirai, Okiko Miyata, Norimitsu Tohnai, Mikiji Miyata, David J.Procter, David Sucunza, Takeaki Naito
    • Journal Title

      J.Org.Chem. 73

      Pages: 4464-4475

    • Related Report
      2010 Final Research Report
  • [Journal Article] Scope of the radical addition-cyclization-elimination reaction of oxime ether towards the synthesis of tricyclic lactam derivatives.2008

    • Author(s)
      Habibur Rahaman, Atsushi Shirai, Okiko Miyata, Takeaki Naito
    • Journal Title

      Tetrahedron Lett. 49

      Pages: 5789-5792

    • Related Report
      2010 Final Research Report
  • [Journal Article] Regioselective Hydroxysulfenylation of a, b-Unsaturated Imines : Enhanced Stability of an Intermediate Radical.2008

    • Author(s)
      Masafumi Ueda, Hideto Miyabe, Hidenori Shimizu, Hisako Sugino, Okiko Miyata, Takeaki Naito
    • Journal Title

      Angew.Chem.Int.Ed. 47

      Pages: 5600-5604

    • Related Report
      2010 Final Research Report
  • [Journal Article] Total Synthesis of (-) -Martinellic Acid via Radical Addition-Cyclization-Elimination Reaction.2008

    • Author(s)
      白井淳
    • Journal Title

      J. Org. Chem. 73

      Pages: 4464-4475

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Scope of the radical addition-cyclization-elimination reaction of oxime ether towards the synthesis of tricyclic lactam derivatives.2008

    • Author(s)
      Habibur Rahaman
    • Journal Title

      Tetrahedron Lett. 49

      Pages: 5789-5792

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Regioselective Hydroxysulfenylation of α, β-Unsaturated Imines : Enhanced Stability of an Intermediate Radical.2008

    • Author(s)
      上田昌史
    • Journal Title

      Angew. Chem. Int. Ed. 47

      Pages: 5600-5604

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] DIRECT SYNTHESIS OF ISOXAZOLES VIA DOMINO REACTION OF ALKYNYL OXIMEETHERS2010

    • Author(s)
      内藤猛章
    • Organizer
      24^<th> European Colloquium on Heterocyclic Chemistry
    • Place of Presentation
      ウィーン(オーストリア)
    • Year and Date
      2010-08-25
    • Related Report
      2010 Annual Research Report
  • [Presentation] DIRECT SYNTHESIS OF ISO XAZOLES VIA DOMINO REACTION OF A LKYNYL OXIME ETHERS2010

    • Author(s)
      内藤猛章
    • Organizer
      24^<th> European Colloquium on Heterocyclic Chemistry
    • Place of Presentation
      ウィーン(オーストリア)
    • Related Report
      2010 Final Research Report
  • [Presentation] Great Oxime Ethers in Radical Reaction2009

    • Author(s)
      内藤猛章
    • Organizer
      The 4th Pacific Symposium on Radical Chemistry
    • Place of Presentation
      上海(中国)
    • Year and Date
      2009-11-20
    • Related Report
      2010 Final Research Report
  • [Presentation] Attractive Oxime Ethers in Radical Reaction2009

    • Author(s)
      内藤猛章
    • Organizer
      The 4th Pacific Symposium on Radical Chemistry
    • Place of Presentation
      上海(中国)
    • Year and Date
      2009-11-20
    • Related Report
      2009 Annual Research Report
  • [Presentation] DOMINO RADICAL REACTIONS OF OXIME ETHERS2009

    • Author(s)
      内藤猛章
    • Organizer
      Organic Free Radicals Ottawa-2009
    • Place of Presentation
      オタワ(カナダ)
    • Year and Date
      2009-07-29
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation]2008

    • Author(s)
      内藤猛章、宮田興子、武田紀彦、影平俊介
    • Organizer
      Benzofuran Synthesis From N-Aryl Oxime Ethers
    • Place of Presentation
      ボルドー(フランス)
    • Year and Date
      2008-09-08
    • Related Report
      2010 Final Research Report
  • [Presentation] 10^<th> International Symposium on Organic Free Radicals2008

    • Author(s)
      内藤猛章
    • Organizer
      3^<rd> Pacific Symposium on Radical Chemistry
    • Place of Presentation
      ヘロン島(オーストラリア)
    • Year and Date
      2008-08-07
    • Related Report
      2010 Final Research Report
  • [Remarks] ホームページ等

    • URL

      http://www.kobepharma-u.ac.jp/rsch/rsch_08.html

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.kobepharma-u.ac.jp/rsch/rsch_08.html

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.kobepharma-u.ac.jp/rsch/rsch_08.html

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://www.kobepharma-u.ac.jp/~medchem/Research/research.html

    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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