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Synthesis and Reaction of N-Allenylimides

Research Project

Project/Area Number 15K07881
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

Sueda Takuya  広島国際大学, 薬学部, 准教授 (40260682)

Co-Investigator(Kenkyū-buntansha) 柳田 玲子  広島国際大学, 薬学部, 教授 (80239821)
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: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
KeywordsN-アレニルイミド / アレニミド / ヘテロ環合成 / N-アルキニルイミド / イニミド / アレナミド / イナミド / 複素環 / ヘテロ環化合物 / ヘテロ環
Outline of Final Research Achievements

Among the heteroatom-substituted alkynes and allenes, those with nitrogen substitutions have become an important building block in modern organic synthesis. In contrast to the well-defined ynamides and allenamides, to date, there are little examples of imide derivatives. We have recently reported the Cu-catalyzed coupling of alkynyl(triaryl)bismuthonium salts with imides to furnish the first reliable synthetic method of ynimides. Now we found a first convenient approach for the synthesis of internal allenimides via silver-mediated isomerization of ynimides. Allenimides could be used as synthetic building units in the synthesis of heterocyclic compounds.

Report

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

    (19 results)

All 2018 2017 2016 2015 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 2 results) Presentation (11 results) Remarks (2 results)

  • [Journal Article] One-pot synthesis of triazole-fused isoindoles from o-alkynylbenzaldehydes and trimethylsilyl azide2018

    • Author(s)
      Okamoto, Noriko; Sueda, Takuya; Minami, Hideki; Yanada, Reiko
    • Journal Title

      Tetrahedron Letters

      Volume: 15 Issue: 15 Pages: 1461-1464

    • DOI

      10.1016/j.tetlet.2018.03.002

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reaction of 2-propargylphenylcarbamates with diphenyliodonium salts via Meyer-Schuster rearrangement2017

    • Author(s)
      Minami, Hideki; Okamoto, Noriko; Sueda, Takuya; Sakaguchi, Takatsugu; Ishikura, Minoru; Yanada, Reiko
    • Journal Title

      Tetrahedron Letters

      Volume: 45 Issue: 45 Pages: 4277-4280

    • DOI

      10.1016/j.tetlet.2017.09.079

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Tandem Decyclization-Cyclization Reaction of N-Alkynyl-3-hydroxyisoindolin-1-ones Generated from N-Alkynyl Phthalimides: Selective Synthesis of ortho-(2-Oxazolyl)phenyl Ketones2016

    • Author(s)
      Sueda, Takuya; Okamoto, Noriko; Yanada, Reiko
    • Journal Title

      Journal of Organic Chemistry

      Volume: 13 Issue: 13 Pages: 5745-5751

    • DOI

      10.1021/acs.joc.6b00888

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regioselective Arylative Ring-Closing Reaction of 2-Alkynylphenyl Derivatives: Formation of Arylated Benzoxazin- 2-ones, Benzoxazin-2-amines and 2,3-Disubstituted Indoles2016

    • Author(s)
      Hideki Minami, Takuya Kanayama, Reishi Tanaka, Noriko Okamoto, Takuya Sueda, Reiko Yanada
    • Journal Title

      Eur. J. Org. Chem.

      Volume: - Issue: 36 Pages: 5990-6000

    • DOI

      10.1002/ejoc.201601162

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Catalyzed Tandem Amide N-Arylation and Regioselective Cyclization od 2-Alkynylbenzamides2016

    • Author(s)
      Hideki Minami, Takuya Sueda, Noriko Okamoto, Yoshihisa Miwa, Minoru Ishikura, Reiko Yanada
    • Journal Title

      Eur. J. Org. Chem.

      Volume: - Issue: 3 Pages: 541-548

    • DOI

      10.1002/ejoc.201501330

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Tandem Reaction of Ethynyl Acetate: Precursor of Allenyl Ketones2016

    • Author(s)
      Noriko Okamoto, Takuya Sueda, reiko Yanada
    • Journal Title

      Chem. Pharm. Bull.

      Volume: 7

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] N-アレニルフタルイミドの環の開裂及び再構築による複素環合成2018

    • Author(s)
      末田拓也,岡本典子,柳田玲子
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] N-アルキニル-3-ヒドロキシイソインドリノンの環開裂反応を利用したオキサゾロンの合成2017

    • Author(s)
      伊藤 醇,末田 拓也,岡本 典子,柳田 玲子
    • Organizer
      日本薬学会第137年会(仙台)
    • Place of Presentation
      仙台国際センター(宮城県仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] α-ヒドロキシイナミドへの1,3-ジカルボニル化合物の位置選択的付加反応を活用する三環性イソインドール誘導体の合成2017

    • Author(s)
      田中 玲詩, 岡本 典子, 末田 拓也, 柳田 玲子
    • Organizer
      日本薬学会第137年会(仙台)
    • Place of Presentation
      仙台国際センター(宮城県仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] N-アレニルフタルイミドの環の開裂と再構築による複素環合成2017

    • Author(s)
      末田拓也,岡本典子,柳田玲子
    • Organizer
      第56回日本薬学会・日本薬剤師会・日本病院薬剤師会 中国四国支部学術大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] N-アレニル-3-ヒドロキシイソインドリノンの環の開裂と再構築による複素環の合成2017

    • Author(s)
      末田拓也,岡本典子,柳田玲子
    • 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] N-アルキニルフタルイミドの環の開裂と再構築を基盤とする複素環の合成研究2016

    • Author(s)
      末田拓也,岡本典子,柳田玲子
    • Organizer
      第42回反応と合成の進歩シンポジウム(静岡)
    • Place of Presentation
      静岡市清水文化会館マリナート(静岡県静岡市)
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
  • [Presentation] N-アルキニル-3-ヒドロキシイソインドリノンの環骨格再構築によるオキサゾロンの合成2016

    • Author(s)
      末田拓也,岡本典子,柳田玲子
    • Organizer
      第55回日本薬学会・日本薬剤師会・日本病院薬剤師会 中国四国支部学術大会(岡山)
    • Place of Presentation
      就実大学(岡山県岡山市)
    • Year and Date
      2016-11-05
    • Related Report
      2016 Research-status Report
  • [Presentation] N-アルキニルフタルイミドの環開裂と環拡大反応によるベンズオキサゼピン骨格の構築2016

    • Author(s)
      南英輝,末田拓也,岡本典子,柳田玲子
    • Organizer
      日本薬学会第136年会(横浜)
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] オルト置換アルキニルベンゼン誘導体の新規タンデム型環化反応の開発2016

    • Author(s)
      金山拓矢,田中玲詩,南英輝,末田拓也,岡本典子,柳田玲子
    • Organizer
      日本薬学会第136年会(横浜)
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] イニミドを活用するベンズオキサゼピン誘導体の合成2015

    • Author(s)
      末田拓也,岡本典子,柳田玲子
    • Organizer
      第54回日本薬学会・日本薬剤師会・日本病院薬剤師会 中国四国支部学術大会(高知)
    • Place of Presentation
      高知市文化プラザかるぽーと(高知県高知市)
    • Year and Date
      2015-10-31
    • Related Report
      2015 Research-status Report
  • [Presentation] 未踏の化学種イニミド及びアレニミドの合成と反応2015

    • Author(s)
      末田拓也,岡本典子,柳田玲子
    • Organizer
      第41回 反応と合成の進歩シンポジウム
    • Place of Presentation
      近畿大学 11月ホール(大阪府東大阪市)
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Remarks] 広島国際大学薬学部薬学科

    • URL

      http://www.hirokoku-u.ac.jp/pharm/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 広島国際大学薬学部薬学科有機薬化学研究室ホームページ

    • URL

      http://www.hirokoku-u.ac.jp/pharm/organic_medicinal/

    • Related Report
      2016 Research-status Report

URL: 

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

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