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Development of novel cascade reactions of alkyne derivatives for the efficient synthetic procedures of heterocycles

Research Project

Project/Area Number 24790024
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
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) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2014: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2013: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsアルキン / 複素環 / 金触媒 / ヨウ素試薬 / ヨウ素 / ニトリル / イミダゾール / イソクロマン / オキサゾール / 超原子価ヨウ素 / クロマン
Outline of Final Research Achievements

We have developed the efficient synthetic methods of heterocyclic compounds by means of cascade reactions and multi-component reactions based on each of the following reactions: 1) syntheses of polycyclic isochromane and benzofuran via Au-catalyzed carboalkoxylation reactions, 2) syntheses of oxazoles and imidazoles by metal-free [2+2+1]annulation reactions, and 3) syntheses of fluorinated oxazoles through hypervalent iodine-mediated cycloisomerization-fluorination reaction.

Report

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

    (31 results)

All 2015 2014 2013 2012 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 1 results,  Acknowledgement Compliant: 4 results) Presentation (16 results) (of which Invited: 2 results) Book (1 results) Remarks (6 results)

  • [Journal Article] Three-Component Synthesis of Indolizines from Azaaromatic-Acethylenedicarboxylate Zwitterions with Acylzirconocene Chloride Complexes.2015

    • Author(s)
      齊藤亜紀夫,山下直樹,須藤耕平,榛澤雄二
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 1 Pages: 108-112

    • DOI

      10.3987/com-14-s(k)22

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Formal N-Acylation Reaction of Azaaromatics with Acylzirconocene Chloride Complexes and 1,1,1,3,3,3-hexafluoroisopropanol (HFIP).2015

    • Author(s)
      齊藤亜紀夫,植松勇樹,須藤耕平,榛澤雄二
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 357 Issue: 5 Pages: 1049-1052

    • DOI

      10.1002/adsc.201401108

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Metal-Free [2+2+1] Annulation of Alkynes, Nitriles and N-Atoms from Iminoiodanes for Synthesis of Highly Substituted Imidazoles.2015

    • Author(s)
      齊藤亜紀夫,神原結衣,柳生琢磨,野口恵一,吉村祥,Viktor V. Zhdankin
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 357 Issue: 4 Pages: 667-671

    • DOI

      10.1002/adsc.201500032

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Catalytic Consecutive Reactions of Alkynes for Syntheses of Heterocycles2014

    • Author(s)
      齊藤亜紀夫,榛澤雄二
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 72 Issue: 3 Pages: 246-256

    • DOI

      10.5059/yukigoseikyokaishi.72.246

    • NAID

      130003395391

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Metal-Free [2 + 2 + 1] Annulation of Alkynes, Nitriles, and Oxygen Atoms: Iodine(III)-Mediated Synthesis of Highly Substituted Oxazoles2013

    • Author(s)
      齊藤亜紀夫,谷口彰啓,神原結衣,榛澤雄二
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 11 Pages: 2672-2675

    • DOI

      10.1021/ol4009816

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Reissert-type Acylation using Acylzirconocene Chloride Complexes2013

    • Author(s)
      齊藤亜紀夫,桜井光,須藤耕平,村井洸介,榛澤雄二
    • Journal Title

      European Journal of Organic Chemistry

      Volume: (32) Issue: 32 Pages: 7295-7299

    • DOI

      10.1002/ejoc.201301264

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Reissert-like Alkenylation of Azaaromatic Compounds with Alkenylzirconocene Chloride Complexes2012

    • Author(s)
      Saito, A.
    • Journal Title

      Heterocycles

      Volume: 86 Issue: 1 Pages: 267-280

    • DOI

      10.3987/com-12-s(n)7

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Highly Substituted Oxazoles through Iodine(III)-Mediated Reactions of Ketones with Nitriles2012

    • Author(s)
      A. Saito, N. Hyodo, Y. Hanzawa
    • Journal Title

      Molecules

      Volume: 17(9) Issue: 9 Pages: 11046-11055

    • DOI

      10.3390/molecules170911046

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] ヨードニウムイオンによる活性化を利用したアルキン-カルボニルメタセシス反応2015

    • Author(s)
      村井洸介,齊藤亜紀夫
    • Organizer
      日本薬学会 第135年会
    • Place of Presentation
      神戸学院大学 (神戸)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 超原子価ヨウ素試薬を用いるアルデヒド誘導体のC-Hアジド化反応2015

    • Author(s)
      篠本雪乃,吉村祥,Viktor V. Zhdankin,齊藤亜紀夫
    • Organizer
      日本薬学会 第135年会
    • Place of Presentation
      神戸学院大学 (神戸)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] プロパルギルアミド誘導体の逐次的環化―フッ素化反応2014

    • Author(s)
      浅利直生,齊藤亜紀夫
    • Organizer
      第37回フッ素化学討論会
    • Place of Presentation
      大阪府立男女共同参画・少年センター (大阪)
    • Year and Date
      2014-10-30 – 2014-10-31
    • Related Report
      2014 Annual Research Report
  • [Presentation] Metal-Free Oxidative Annulation of Alkynes, Nitriles, and Heteroatoms2014

    • Author(s)
      齊藤亜紀夫,神原結衣
    • Organizer
      4th International Conference on Hypervalent Iodine Chemistry (ICHIC2014)
    • Place of Presentation
      ヒルトン成田ホテル(千葉)
    • Year and Date
      2014-07-02 – 2014-07-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] 1,4-ジイン類とアルデヒドとのメタセシス反応を経由するフラン合成法2014

    • Author(s)
      村井洸介,齊藤亜紀夫
    • Organizer
      日本薬学会 第134年会
    • Place of Presentation
      熊本大学 (熊本)
    • Related Report
      2013 Research-status Report
  • [Presentation] 逐次的カルボアルコキシレーション-付加反応による多環性イソクロマン合成2014

    • Author(s)
      小幡智之,齊藤亜紀夫
    • Organizer
      日本薬学会 第134年会
    • Place of Presentation
      熊本大学 (熊本)
    • Related Report
      2013 Research-status Report
  • [Presentation] 三価ヨウ素試薬を用いる[2+2+1]環形成反応を利用した複素環合成法2013

    • Author(s)
      齊藤亜紀夫, 神原結衣, 谷口彰啓, 榛澤雄二
    • Organizer
      第103回 有機合成化シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部マルチメディア講堂(東京)
    • Related Report
      2013 Research-status Report
  • [Presentation] メタルフリーな環化付加型反応を利用する複素環合成2013

    • Author(s)
      齊藤亜紀夫, 神原結衣, 谷口彰啓, 榛澤雄二
    • Organizer
      第43回 複素環化学討論会
    • Place of Presentation
      長良川国際会議場 (岐阜)
    • Related Report
      2013 Research-status Report
  • [Presentation] メタルフリーな [2+2+1] 環形成反応を利用したイミダゾール合成2013

    • Author(s)
      神原結衣,齊藤亜紀夫
    • Organizer
      第39回 反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部百年講堂 (福岡)
    • Related Report
      2013 Research-status Report
  • [Presentation] アシルジルコノセンクロリド錯体を用いるピロロ[2,1-a]イソキノリン合成2013

    • Author(s)
      齊藤 亜紀夫, 山下 直樹, 榛澤 雄二
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川)
    • Related Report
      2012 Research-status Report
  • [Presentation] プロパルギルアミン誘導体とカルボニル化合物からの触媒的ピロール合成2013

    • Author(s)
      合屋 雄太, 榛澤 雄二, 齊藤 亜紀夫
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川)
    • Related Report
      2012 Research-status Report
  • [Presentation] 三価ヨウ素試薬を用いるアルキンとニトリルからのイミダゾール合成2013

    • Author(s)
      神原 結衣, 榛澤 雄二, 齊藤 亜紀夫
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川)
    • Related Report
      2012 Research-status Report
  • [Presentation] 三価ヨウ素試薬を用いるアルキンとニトリルからの分子間オキサゾール合成法2012

    • Author(s)
      齊藤 亜紀夫, 谷口 彰啓, 兵頭 菜緒, 榛澤 雄二
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      タワーホール船堀(東京)
    • Related Report
      2012 Research-status Report
  • [Presentation] Iodine(III)-Mediated [2+2+1] cycloaddition of Alkynes, Nitriles and Oxygen Atoms2012

    • Author(s)
      齊藤 亜紀夫, 谷口 彰啓, 兵頭 菜緒, 榛澤 雄二
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都(京都)
    • Related Report
      2012 Research-status Report
  • [Presentation] アルキン化合物の連続反応を利用した触媒的複素環合成法

    • Author(s)
      齊藤 亜紀夫
    • Organizer
      千葉大学 第3回 化学系若手研究者講演会
    • Place of Presentation
      千葉大学亥鼻キャンパス(千葉)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 効率的複素環合成法を指向したアルキン化合物の連続反応

    • Author(s)
      齊藤 亜紀夫
    • Organizer
      立命館大学薬学部 創薬基盤化学研究若手セミナー
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス (滋賀)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Book] Stereoselective Synthesis of Drugs and Natural Products(24章,Metathesis Reactions in Drug and Natural Product Synthesis)2013

    • Author(s)
      齊藤亜紀夫,榛澤雄二
    • Total Pages
      1836
    • Publisher
      John Wiley & Sons
    • Related Report
      2013 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://www.tuat.ac.jp/~akio-sai/index.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 東京農工大学 研究者情報(齊藤亜紀夫のページ)

    • URL

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

    • Related Report
      2014 Annual Research Report
  • [Remarks] 東京農工大学 テニュアトラック教員の紹介(齊藤亜紀夫のページ)

    • URL

      http://www.tenure-track-tuat.org/scholar/technology/post_16.html

    • Related Report
      2014 Annual Research 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://www.tuat.ac.jp/~akio-sai/index.html

    • Related Report
      2013 Research-status Report
  • [Remarks] 東京農工大学 テニュアトラック教員の紹介

    • URL

      http://www.tenure-track-tuat.org/scholar/technology/post_16.html

    • Related Report
      2013 Research-status Report
  • [Remarks] 東京農工大学 研究者プロフィール

    • URL

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

    • Related Report
      2013 Research-status Report

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

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