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Development of domino reactions utilizing unique property of N-alkoxy-amides and imines

Research Project

Project/Area Number 24590039
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

UEDA Masafumi  神戸薬科大学, 薬学部, 准教授 (00340935)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsドミノ反応 / ラジカル / オキシム / ヒドラゾン / ヘテロ環 / 遷移金属触媒 / ラジカル反応 / Fischerインドール合成 / 共役ヒドラゾン / 複素環合成 / Weinreb アミド / イソキサゾール / 共役イミン
Outline of Final Research Achievements

Domino reactions are greener reactions that allow for complex molecules to be constructed from a simple substrate in one operation in a straightforward, efficient, and elegant way without isolation of intermediates. The domino reaction of O-phenyl-conjugated oxime ether with an alkyl radical allows the construction of two heterocycles with three stereogenic centers as a result of the formation of two C-C bonds, a C-O bond, and a C-N bond in a single operation, leading to benzofuro[2,3-b]pyrroles, which are not easily accessible by existing synthetic methods. In addition, we also developed that a new method for the synthesis of isoquinolinones involving the palladium-catalyzed cyclization reaction.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (21 results)

All 2015 2014 2013 2012 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 2 results,  Acknowledgement Compliant: 2 results) Presentation (15 results) (of which Invited: 2 results) Remarks (1 results)

  • [Journal Article] Direct Synthesis of Benzofuro[2,3-b]pyrroles through a Radical Addition/[3,3]-Sigmatropic Rearrangement/Cyclization/Lactamization Cascade2014

    • Author(s)
      Masafumi Ueda, Yuta Ito, Yuki Ichii, Maiko Kakiuchi, Hiroko Shono and Okiko Miyata
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 22 Pages: 6763-6770

    • DOI

      10.1002/chem.201402217

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Sequential Radical Addition and Fischer-Type Indolization Reactions of Conjugated Hydrazones for the Preparation of a-Alkylindole-3-Acetic Acids2014

    • Author(s)
      Yuta Ito, Masafumi Ueda, Naomi Matsuda, Yuika Nishida, and Okiko Miyata
    • Journal Title

      Heterocycles

      Volume: 89 Issue: 4 Pages: 963-969

    • DOI

      10.3987/com-14-12957

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Synthesis of Isoquinolinones via Sequential Cyclization and N-O Bond Cleavage of N-Methoxy-o-alkynylbenzamides2013

    • Author(s)
      Manita Jithunsa, Masafumi Ueda, Naoki Aoi, Shoichi Sugita, Tetsuya Miyoshi and Okiko Miyata.
    • Journal Title

      Synlett

      Volume: (4) Issue: 04 Pages: 475-478

    • DOI

      10.1055/s-0032-1318159

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Penmacric Acids via an Intermolecular Radical Addition Reaction2013

    • Author(s)
      Masafumi Ueda, Ayako Ono, Dai Nakao, Kenji Matsuno, Takeaki Naito and Okiko Miyata
    • Journal Title

      Tetrahedron

      Volume: 69(33) Issue: 33 Pages: 6866-6874

    • DOI

      10.1016/j.tet.2013.06.006

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Synthesis of Trisubstituted Isoxazoles via a Cascade Cyclization-Migration Process2012

    • Author(s)
      Masafumi Ueda, Shoichi Sugita, Aoi Sato, Tetsuya Miyoshi, and Okiko Miyata
    • Journal Title

      J. Org. Chem.

      Volume: 77 Issue: 20 Pages: 9344-9351

    • DOI

      10.1021/jo301358h

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 共役イミン類のドミノ型反応2015

    • Author(s)
      上田昌史
    • Organizer
      創薬基盤化学研究第10回若手セミナー特別講演会
    • Place of Presentation
      草津
    • Year and Date
      2015-02-03
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Synthesis of N-bridged heterocycles via Au-catalyzed cyclization-cycloaddition reaction of a-alkynyl oxime ether2014

    • Author(s)
      Masafumi Ueda, Shoichi Sugita, Makoto Saito, Norihiko Takeda, Kenji Matsuno, Okiko Miyata
    • Organizer
      The Ninth International Symposium on Integrated Synthesis (ISIS-9)
    • Place of Presentation
      淡路
    • Year and Date
      2014-11-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] Regioselective Ring-Opening Reaction of Trichloromethylcyclopropanes2014

    • Author(s)
      Masafumi Ueda, Nobuyoshi Doi, Norihiko Takeda, Okiko Miyata
    • Organizer
      The Ninth International Symposium on Integrated Synthesis (ISIS-9)
    • Place of Presentation
      淡路
    • Year and Date
      2014-11-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] トリクロロメチル基を有するシクロプロパン類の位置選択的開環反応の開発2014

    • Author(s)
      上田昌史、土井信佳、武田紀彦、宮田興子
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] アルキニルオキシムエーテル類の金触媒によるドミノ型閉環-環化付加反応の開発2014

    • Author(s)
      上田昌史、齋藤誠、杉田翔一、武田紀彦、宮田興子
    • Organizer
      第64回日本薬学会近畿支部総会・大会
    • Place of Presentation
      京都
    • Year and Date
      2014-10-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] アルキニルオキシムエーテル類の閉環-環化付加反応による架橋型含窒素複素環の合成2014

    • Author(s)
      上田昌史、杉田翔一、齋藤誠、武田紀彦、宮田興子
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2014-09-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] アルキンを有するオキシムエーテル類を基質とした新規ドミノ型閉環―環化付加反応の開発2014

    • Author(s)
      上田昌史、杉田翔一、齋藤誠、武田紀彦、宮田興子
    • Organizer
      第34回有機合成若手セミナー
    • Place of Presentation
      豊中
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] 共役イミン類への付加反応を基盤とするドミノ型反応の開発2014

    • Author(s)
      上田昌史
    • Organizer
      第34回有機合成若手セミナー
    • Place of Presentation
      豊中
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Regioselective Cyclization of 2-Alkynyl-methoxybenzamides2014

    • Author(s)
      Masafumi Ueda, Manita Jithunsa、Naoki Aoi, Shoichi Sugita, Tetsuya Miyoshi, Okiko Miyata
    • Organizer
      The 20th International Conference on Organic Synthesis (ICOS-20)
    • Place of Presentation
      Budapest
    • Year and Date
      2014-06-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] Direct Synthesis of Benzofuro[2,3-b]pyrroles by a Domino Reaction Involving a Radical Addition and [3,3]-Sigmatropic Rearrangement2014

    • Author(s)
      Masafumi Ueda, Yuta Ito, Okiko Miyata
    • Organizer
      The 20th International Conference on Organic Synthesis (ICOS-20)
    • Place of Presentation
      Budapest
    • Year and Date
      2014-06-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] ラジカル付加反応と[3,3]-シグマトロピー転位が連動するドミノ型反応の開発2014

    • Author(s)
      伊藤勇太、上田昌史、宮田興子
    • Organizer
      第12回次世代を担う有機化学シンポジウム
    • Place of Presentation
      渋谷
    • Year and Date
      2014-05-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of Isoxazoles via Transition Metal-Catalyzed Domino Reaction of Alkynyl Oxime Ethers2012

    • Author(s)
      Masafumi Ueda, Aoi Sato, Shoichi Sugita, Tetsuya Miyoshi and Okiko Miyata
    • Organizer
      Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] アルキニルオキシムエーテル類の金触媒によるドミノ型閉環-環化付加反応の開発

    • Author(s)
      上田昌史、杉田翔一、山口みなみ、三好哲也、宮田興子
    • Organizer
      第63回日本薬学会近畿支部総会・大会
    • Place of Presentation
      京都
    • Related Report
      2013 Research-status Report
  • [Presentation] ドミノ型ラジカル付加-転位反応を利用したベンゾフロ[2,3-b]ピロールの合成

    • Author(s)
      上田昌史、伊藤勇太、三好哲也、宮田興子
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      岐阜
    • Related Report
      2013 Research-status Report
  • [Presentation] ベンゾフロ [2,3-b] ピロール骨格の効率的合成法の開発

    • Author(s)
      上田昌史、伊藤勇太、三好哲也、宮田興子
    • Organizer
      第31回メディシナルケミストリーシンポジウム
    • Place of Presentation
      広島
    • Related Report
      2013 Research-status Report
  • [Remarks] 神戸薬科大学薬品化学研究室

    • URL

      http://www.kobepharma-u.ac.jp/medchem/index.html

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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