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New development of cycloaddition reactions using cyclobutanones

Research Project

Project/Area Number 15K07855
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKanazawa University

Principal Investigator

Matsuo Jun-ichi  金沢大学, 薬学系, 教授 (50328580)

Co-Investigator(Renkei-kenkyūsha) YOSHIMURA Tomoyuki  金沢大学, 医薬保健研究域薬学系, 准教授 (20432320)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsシクロブタノン / 付加環化 / 環化付加反応 / 結合開裂 / 有機合成 / 反応開発 / 炭素ー炭素結合 / 環化付加
Outline of Final Research Achievements

1,4-Zwitterionic intermediates which were generated by activation of 3-ethoxycyclobutanones with an appropriate Lewis acid reacted with azobenzenes, quinolines, isoquinolines, ynamides, nitrosobenzenes, and reactive alkynes gave the corresponding 6-membered cyclic compounds by formal [4+2] cycloaddition reactions. A zwitterionic intermediate generated from 3-phenylcyclobutanones reacted aromatics to afford Friedel-Crafts adducts. Also, an adduct between 1,4-ketoaldehyde and tosylhydrazine rected with nucleophiles under activation with a Lewis acid to give dihydropyridazines.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (26 results)

All 2018 2017 2016 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Acknowledgement Compliant: 4 results) Presentation (15 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results) Remarks (3 results)

  • [Journal Article] Friedel-Crafts Alkylation of Aromatics by TiCl4-Promoted Ring Cleavage of 3-Arylcyclobutanones2018

    • Author(s)
      Kanie, M.; Yoshimura, T.; Matsuo, J.
    • Journal Title

      Synthesis

      Volume: 50 Issue: 03 Pages: 548-554

    • DOI

      10.1055/s-0036-1591497

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reactions of Nitrosobenzenes with Cyclobutanones by Activation with Lewis Acid2018

    • Author(s)
      Shima, Y.; Iagarashi, E.; Yoshimura, T.; Matsuo, J.
    • Journal Title

      Synlett

      Volume: 29 Issue: 06 Pages: 723-726

    • DOI

      10.1055/s-0036-1588469

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of multisubstituted phenols by formal [4 + 2] cycloaddition of nucleophilic alkynes with 3-ethoxycyclobutanones2017

    • Author(s)
      Kuzuguchi Takeo、Yabuuchi Yuto、Yoshimura Tomoyuki、Matsuo Jun-ichi
    • Journal Title

      Org. Biomol. Chem.

      Volume: 15 Issue: 25 Pages: 5268-5271

    • DOI

      10.1039/c7ob00827a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of various 6-substituted 1,4,5,6-tetrahydropyridazines by substitution of a 1,4,5,6-tetrahydro-6-tosylhydrazinopyridazines2017

    • Author(s)
      Shunya Morita and Jun-ichi Matsuo
    • Journal Title

      Tetrahedron Lett.

      Volume: 58 Issue: 10 Pages: 932-934

    • DOI

      10.1016/j.tetlet.2017.01.069

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Formal [4+2] Cycloaddition of Quinolines, Pyridines, and Isoquinolines with 3-Ethoxycyclobutanones2016

    • Author(s)
      Tatsuo Onnagawa, Yusuke Shima, Tomoyuki Yoshimura, and Jun-ichi Matsuo
    • Journal Title

      Tetrahedron Lett.

      Volume: 57 Issue: 27-28 Pages: 3050-3052

    • DOI

      10.1016/j.tetlet.2016.06.011

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Formal [4+2] cycloaddition of 3-ethoxycyclobutanones with azo compounds2016

    • Author(s)
      Yusuke Shima and Jun-ichi Matsuo
    • Journal Title

      Tetrahedron Lett.

      Volume: 57 Issue: 36 Pages: 4066-4069

    • DOI

      10.1016/j.tetlet.2016.07.087

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of alpha-halo-gamma-hydroxyenamides by titanium tetrahalide-mediated addition of aldehydes or ketones to ynamides2016

    • Author(s)
      Yuto Yabuuchi, Takeo Kuzuguchi, Tomoyuki Yoshimura, and Jun-ichi Matsuo*
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 19 Pages: 4951-4953

    • DOI

      10.1021/acs.orglett.6b02526

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 3位にドナー型置換基を有するシクロブタノンのルイス酸による活性化と形式的環化付加反応の開発2016

    • Author(s)
      松尾淳一
    • Journal Title

      有機合成化学協会誌

      Volume: 74

    • NAID

      130005164593

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Development of Cycloaddition Reactions Using 1,4-Zwitterionic Intermediates2018

    • Author(s)
      Junichi Matsuo
    • Organizer
      4th European Organic Chemsitry Congress
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 3-エトキシシクロブタノンとシロキシジエンとの形式的[4+4]付加環化反応の開発2018

    • Author(s)
      西優奈、吉村智之、松尾淳一
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] アレニルシランと3-エトキシシクロブタノンとの反応による[3.2.1]オキサビシクロヘプタノン環骨格の構築法開発2018

    • Author(s)
      女川起生、吉村智之、松尾淳一
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] α-ハロ-γ-ヒドロキシエナミドの新しい合成法と分子内環化反応の開発2017

    • Author(s)
      〇藪内優斗、葛口岳生、松尾淳一
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] シクロブタノンと芳香環化合物とのFriedel-Crafts反応の開発2017

    • Author(s)
      〇蟹江真悠、吉村智之、松尾淳一
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] ルイス酸活性化によるシクロブタノンとニトロソベンゼンとの反応2017

    • Author(s)
      嶋佑介、〇五十嵐笑子、吉村智之、松尾淳一
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Development of Cycloaddition Reactions Using 1,4-Zwitterionic Intermediates2017

    • Author(s)
      Junichi Matsuo
    • Organizer
      The 34th Seminar on Synthetic Organic Chemistry
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 水酸基支配による幾何異性選択的パラジウム触媒反応2017

    • Author(s)
      藪内優斗、吉村智之、松尾淳一
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 分子内Diels-Alder反応によるallocolchicine類縁体合成研究2017

    • Author(s)
      花島美香、吉村智之、松尾淳一
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 新しいヒドロピリダジン供与体と合成反応の開発2016

    • Author(s)
      〇森田瞬也、松尾淳一
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢
    • Year and Date
      2016-09-26
    • Related Report
      2016 Research-status Report
  • [Presentation] ピリジンまたはキノリン誘導体と3-エトキシシクロブタノンとの形式的[4+2]環化付加反応2016

    • Author(s)
      女川起生、嶋佑介、松尾淳一
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 四塩化チタンを用いるイナミンとアルデヒドまたはケトンとの反応2016

    • Author(s)
      藪内優斗、葛口岳生、松尾淳一
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] N―トシルイナミドと3-エトキシシクロブタノンとの形式的[4+2]環化付加反応の開発2016

    • Author(s)
      葛口岳生、松尾淳一
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] α-ハロ-γ-ヒドロキシエナミドの新しい合成法の開発とその有用性2016

    • Author(s)
      〇藪内優斗、葛口岳生、吉村智之、松尾淳一
    • Organizer
      日本薬学会北陸支部第128回例会
    • Place of Presentation
      金沢
    • Related Report
      2016 Research-status Report
  • [Presentation] 多様なテトラヒドロピリダジン類の新しい合成法の開発2016

    • Author(s)
      〇森田瞬也、松尾淳一
    • Organizer
      日本薬学会北陸支部第128回例会
    • Place of Presentation
      金沢
    • Related Report
      2016 Research-status Report
  • [Remarks] http://www.p.kanazawa-u.ac.jp/~gousei/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 金沢大学薬学 機能性分子合成学

    • URL

      http://www.p.kanazawa-u.ac.jp/~gousei/

    • Related Report
      2016 Research-status Report
  • [Remarks] 金沢大学 薬学 機能性分子合成学

    • URL

      http://www.p.kanazawa-u.ac.jp/~gousei/

    • Related Report
      2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

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