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The development of iodine-catalysis without terminal oxidant and its application to synthesis of heterocycles

Research Project

Project/Area Number 18K06573
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionTokyo University of Agriculture and Technology

Principal Investigator

SAITO Akio  東京農工大学, 工学(系)研究科(研究院), 准教授 (10339103)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsヨウ素 / 触媒 / メタルフリー / 複素環化合物 / アルキン / ピロール / インドール / 環化反応 / ピロリジン / フラン / 環化付加反応 / ピラン / 複素環
Outline of Final Research Achievements

As a solution to problems (scarcity, toxicity and others) of the metal catalyst frequently used in organic syntheses, the organic synthetic methods have been developed by using of less toxic and safe organic iodine reagents, which have a variety of reactivities. However, many of these methods have been focused on hypervalent iodine catalyst generated from organic iodine reagents and terminal oxidants, and the applicable synthetic methods have been limited. Through this study using the iodine catalyst system without terminal oxidants, novel and metal-free methods have been developed for the various kinds of synthesis of heterocycles.

Academic Significance and Societal Importance of the Research Achievements

ヨウ素は国内で自給可能であり、豊富に存在する元素資源であるため、本研究における「ヨウ素試薬の新しい活用法」は、今後の環境調和型有機合成研究おいて有益な知見を提供し、ファインケミカルズとして実用化が可能であれば日本の産業界に与える影響は絶大である。さらに、本研究の標的化合物は生理活性物質などに見られる有用性や重要性の高い複素環化合物である点から、本研究は物質供給の面でも、医薬品化学などの他分野へ大きく貢献するであろう。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (19 results)

All 2021 2020 2019 2018 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (10 results) (of which Int'l Joint Research: 2 results) Remarks (2 results)

  • [Journal Article] Synthesis of α-(aminoethyl)-α,β-enones via alkyne aza-Prins cyclization and their synthetic application to pyrrolidines2021

    • Author(s)
      Amemiya Sho、Okemoto Shingo、Tsubouchi Akira、Saito Akio
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 19 Issue: 13 Pages: 2959-2967

    • DOI

      10.1039/d1ob00072a

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] BF3-Catalyzed Skeletal Rearrangement of 7-En-2-ynones to endo-Type Cyclic Dienes2020

    • Author(s)
      Daisuke Sato, Yuichiro Watanabe, Keiichi Noguchi, Junichiro Kanazawa, Kazunori Miyamoto, Masanobu Uchiyama
    • Journal Title

      Organic Letters

      Volume: - Issue: 11 Pages: 4063-4067

    • DOI

      10.1021/acs.orglett.0c00949

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hypervalent Iodine-mediated/Catalyzed Oxidative Cycloisomerization/Annulation of Alkynes for Metal-free Synthesis of Oxazoles2020

    • Author(s)
      Saito Akio
    • Journal Title

      Current Organic Chemistry

      Volume: 24 Issue: 18 Pages: 2048-2069

    • DOI

      10.2174/1385272824999200510232438

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Alkyne aza-Prins cyclization of N-(hexa-3,5-diynyl)tosylamides with aldehydes using triflic acid and a binuclear aluminum complex2019

    • Author(s)
      Kobayashi Naoko、Kaneko Kazuma、Amemiya Sho、Noguchi Keiichi、Yamanaka Masahiro、Saito Akio
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 59 Pages: 8619-8622

    • DOI

      10.1039/c9cc03700d

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Formal [2+2+1] Synthesis of Tetrasubstituted Furans from Aldehydes, Acetylenedicarboxylates, and Acyl Compounds2019

    • Author(s)
      Tateishi Keiichiro、Matsumoto Yuri、Saito Akio
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2019 Issue: 33 Pages: 5603-5609

    • DOI

      10.1002/ejoc.201900806

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Domino Synthesis of 2,3-Dialkylidenetetrahydrofurans via Tandem Prins Cyclization?Skeletal Reorganization2018

    • Author(s)
      Kato Mizuki、Saito Akio
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 15 Pages: 4709-4712

    • DOI

      10.1021/acs.orglett.8b02114

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] 2-Picoline catalyst-triggered [2 + 2 + 2] cycloaddition-type reaction of acetylenedicarboxylates, aldehydes and alkenes2018

    • Author(s)
      Tateishi Keiichiro、Noguchi Keiichi、Saito Akio
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 16 Issue: 33 Pages: 5965-5968

    • DOI

      10.1039/c8ob01774c

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] AlCl3-Mediated Cycloisomerization of n-Ene-2-ynones for Synthesis of Bicyclo[3.1.0]hexenes2020

    • Author(s)
      Daisuke Sato, Akio Saito
    • Organizer
      The 14th International Symposium on Organic Reactions (ISOR-14)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] n-エン-2-イノン類の環化異性化反応による複素環合成法2020

    • Author(s)
      佐藤大介, 齊藤亜紀夫
    • Organizer
      第49回 複素環化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Bronsted酸触媒によるエンイノン類からのビシクロ[3.2.0]へプタン合成法2020

    • Author(s)
      青山慎治, 佐藤大介, 坪内彰, 齊藤亜紀夫
    • Organizer
      日本薬学会 第141年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Nonmetal-Catalyzed Skeletal Reorganization of 7-En-2-ynones into 3-Alkylidenecyclohexenes2019

    • Author(s)
      Daisuke Sato, Akio Saito
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Alkyne aza-Prins環化反応を基軸とする共役エノン合成と複素環合成法への応用2019

    • Author(s)
      雨宮将, 桶本慎吾, 齊藤亜紀夫
    • Organizer
      第78回有機合成化学協会関東支部シンポジウム
    • Related Report
      2019 Research-status Report
  • [Presentation] 7-エン-2-イノン誘導体の環化異性化反応によるビシクロ[3.1.0]ヘキサン合成2019

    • Author(s)
      佐藤大介, 齊藤亜紀夫
    • Organizer
      日本薬学会 第140年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 共役ジイニルアミド誘導体のAza-Prins環化反応2018

    • Author(s)
      小林菜穂子、齊藤亜紀夫
    • Organizer
      第114 回有機合成シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] 非金属系触媒によるエンイン環化異性化反応を利用した3-アルキリデンシクロヘキセン合成2018

    • Author(s)
      佐藤大介、齊藤亜紀夫
    • Organizer
      第76回有機合成化学協会関東支部シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] メタルフリーな形式的[2+2+1]環形成型フラン合成法2018

    • Author(s)
      松本優里、立石惠一郎、齊藤亜紀夫
    • Organizer
      日本薬学会 第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 非金属系酸触媒による7-エン-2-イノン誘導体の環化異性化反応2018

    • Author(s)
      佐藤大介、齊藤亜紀夫
    • Organizer
      日本薬学会 第139年会
    • Related Report
      2018 Research-status Report
  • [Remarks] 東京農工大学工学部応用分子化学科 齊藤研究室

    • URL

      http://web.tuat.ac.jp/~akio-sai/index.html

    • Related Report
      2020 Annual Research Report 2019 Research-status Report 2018 Research-status Report
  • [Remarks] 齊藤 亜紀夫 - 研究者プロフィール

    • URL

      http://kenkyu-web.tuat.ac.jp/Profiles/44/0004321/profile.html

    • Related Report
      2020 Annual Research Report 2019 Research-status Report 2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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