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Synthesis of Heterocyclic Compounds via Decarbonylative Cycloadditions

Research Project

Project/Area Number 21750040
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

KURAHASHI Takuya  Kyoto University, 工学研究科, 助教 (50432365)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords複素環 / 触媒反応 / 遷移金属 / ニッケル / 環化付加反応 / 脱カルボニル
Research Abstract

The transition metal-catalyzed insertion reaction of an unsaturated carbon-carbon bond into a carbon-hetero atom bond of an heterocyclic compound is a useful transformation to prepare a more complicated heterocyclic compounds in a single step. However, there is no precedent for such a potentially valuable methodology. We postulated that oxidative addition of cyclic carbonyl compounds to nickel(0) and subsequent decarbonylation are facile and might allow insertion of alkynes. Thus, we developed the decarbonylative addition of anhydrides to alkynes using nickel(0) catalyst to form hetero cyclic compounds, which displays a wide range of biological activities.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (45 results)

All 2011 2010 2009

All Journal Article (25 results) (of which Peer Reviewed: 25 results) Presentation (20 results)

  • [Journal Article] Nickel-catalyzed intermolecular codimerization of acrylates and alkynes.2011

    • Author(s)
      Horie, H.Kurahashi, T.Matsubara, S.
    • Journal Title

      Chem.Commun. 47

      Pages: 2658-2661

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Decarbonylative Cycloaddition of Phthalic Anhydrides with Allenes.2011

    • Author(s)
      Ochi, Y.Kurahashi, T.Matsubara, S.
    • Journal Title

      Org.Lett. 13

      Pages: 1374-1376

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cycloadditions of Thiophthalic Anhydrides with Alkynes.2011

    • Author(s)
      Inami, T.Kurahashi, T.Matsubara, S.
    • Journal Title

      Org.Lett. 13

      Pages: 1912-1915

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cycloaddition of Anthranilic Acid Derivatives to Alkynes.2011

    • Author(s)
      Maizuru, N.Inami, T.Kurahashi, T.Matsubara, S.
    • Journal Title

      Org.Lett. 13

      Pages: 1206-1208

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed Cycloadditions of Benzoxazinones with Alkynes: Synthesis of Quinolines and Quinolones.2011

    • Author(s)
      Maizuru, N.Inami, T.Kurahashi, T.Matsubara, S.
    • Journal Title

      Chem.Lett. 40

      Pages: 375-377

    • NAID

      10028170524

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzedDecarbonylativeCycloadditionof PhthalicAnhydrideswith1,3-Dienes.2011

    • Author(s)
      Fujiwara, K.Kurahashi, T.Matsubara, S.
    • Journal Title

      Chem.Lett. 40

      Pages: 322-325

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed [2+2+1] cycloaddition of alkynes, acrylates and isocyanates.2011

    • Author(s)
      Ozawa, T.Horie, H.Kurahashi, T.Matsubara, S.
    • Journal Title

      Chem.Commun. 40

      Pages: 8055-8057

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Selective synthesis of trienes and dienes via nickel-catalyzed intermolecular Cotrimerization of Acrylates and Alkynes.2011

    • Author(s)
      Horie, H.Kurahashi, T.Matsubara, S.
    • Journal Title

      Chem.Commun. 40

      Pages: 7229-7230

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed Cycloadditions of Benzoxazinones with Alkynes : Synthesis of Quinolines and Quinolones2011

    • Author(s)
      Nobuyoshi Maizuru, Tasuku Inami, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Chem.Lett.

      Volume: 40 Pages: 375-377

    • NAID

      10028170524

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed intermolecular codimerization of acrylates and alkynes2011

    • Author(s)
      Hiroaki Horie, Ichiro Koyama, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Chem.Comm.

      Volume: 47 Pages: 2658-2660

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cycloaddition of Anthranilic Acid Derivatives to Alkynes2011

    • Author(s)
      Nobuyoshi Maizuru, Tasuku Inami, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 1206-1209

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Decarbonylative Cycloaddition of Phthalic Anhydrides with Allenes2011

    • Author(s)
      Yosuke Ochi, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 1374-1377

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cycloadditions of Thiophthalic Anhydrides with Alkynes2011

    • Author(s)
      Tasuku Inami, Yoko Baba, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Org.Lett.

      Volume: 13(受理済 印刷中)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Decarbonylative cycloaddition of phthalimides with 1,3-dienes.2010

    • Author(s)
      Fujiwara, K.Kurahashi, T.Matsubara, S.
    • Journal Title

      Org.Lett 12

      Pages: 4548-4550

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed [4+2] cycloaddition of alkynes to carbonylsalicylamides via elimination of isocyanates.2010

    • Author(s)
      Yoshino, Y.Kurahashi, T.Matsubara, S.
    • Journal Title

      Chem. Lett. 39

      Pages: 896-897

    • NAID

      10027184265

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed [2+2+1] cycloaddition of alkynes, acrylates and isocyanates2010

    • Author(s)
      Takuya Ozawa, Hiroaki Horie, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Chem.Comm.

      Volume: 46 Pages: 8055-8056

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed Decarbonylative Cycloadditionof Phthalic Anhydrides with 1,3-Dienes2010

    • Author(s)
      Kyohei Fujiwara, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Chem.Lett.

      Volume: 40 Pages: 322-323

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective synthesis of trienes and dienes via nickel-catalyzed intermolecular cotrimerization of acrylates and alkynes2010

    • Author(s)
      Hiroaki Horie, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Chem.Comm.

      Volume: 46 Pages: 7229-7231

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed[4+2] Cycloadditionof Alkynes To Carbonylsalicylamides via Elimination of Isocyanates2010

    • Author(s)
      Yasufumi Yoshino, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Chem.Lett.

      Volume: 38 Pages: 896-897

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Decarbonylative Cycloaddition of Phthalimides with 1,3-Dienes2010

    • Author(s)
      Kyohei Fujiwara, Takuya Kurahashi, Seijiro Matsubara
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 4548-4551

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed cycloaddition of salicylic acid ketals to alkynes via elimination of ketones. J. Am.2009

    • Author(s)
      Ooguri, A.Nakai, K.Kurahashi, T.Matsubara, S.
    • Journal Title

      Chem.Soc. 131

      Pages: 13194-13195

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-catalyzed decarboxylative carboamination of alkynes with isatoic anhydrides.2009

    • Author(s)
      Yoshino, Y.Kurahashi, T.Matsubara, S.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 7494-7495

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Cycloaddition of Salicylic Acid Ketals to Alkynes via Elimination of Ketones2009

    • Author(s)
      Ooguri, A.; Nakai, K.; Kurahashi, *T.; Matsubara, *S.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 13194-13195

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Decarboxylative Carboamination of Alkynes with Isatoic Anhydrides2009

    • Author(s)
      Yoshino, Y.; Kurahashi, *T.; Matsubara, *S.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 7494-7495

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed [4+2] Cycloaddition of Enones with Alkynes2009

    • Author(s)
      Koyama, I.; Kurahashi, *T.; Matsubara, *S.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 1350-1351

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] メチレンシクロプロパンをC1合成素子として用いたニッケル触媒による無水チオフタル酸との環化付加反応2011

    • Author(s)
      井波輔、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] ニッケル触媒を利用したo-ハロアニリンとアルキンの環化付加反応によるインドール環合成2011

    • Author(s)
      吉田有次、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] オキシムとアルキンの炭素-水素結合の活性化を伴った環化付加反応によるイソキノリン環合成2011

    • Author(s)
      吉田裕志、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] 無水フタル酸とアルキンの脱カルボニルを伴った位置選択的環化付加反応によるイソクマリン環合成2011

    • Author(s)
      芝隆宏、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] コバルトポルフィリン触媒を用いたジエンとイミンの[4+2]型環化付加反応2011

    • Author(s)
      若林亮太、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] マンガンポルフィリン触媒を用いたエンインの環化異性化反応2011

    • Author(s)
      小澤卓也、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] 二つの炭素.炭素結合の活性化を伴うタンデム反応によるクマリン環合成2011

    • Author(s)
      中井健一朗、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] 鉄ポルフィリン触媒を用いたジエンとアルデヒドの[4+2]型環化付加反応2011

    • Author(s)
      藤原恭平、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] ニッケル触媒によるジエンとアルキンの環化付加反応を用いたビシクロ環合成2011

    • Author(s)
      堀江宏彰、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] Nickel-Catalyzed Cycloadditions of Benzoxazinones with Alkynes : Divergent Synthesis of Quinolines, Quinolones and Indoles.2010

    • Author(s)
      倉橋拓也、松原誠二郎
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学多摩キャンパス
    • Year and Date
      2010-09-18
    • Related Report
      2010 Final Research Report
  • [Presentation] 分子置換型環化付加反応を用いたキノリンおよびキノロン、インドール合成法の開発2010

    • Author(s)
      倉橋拓也
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学多摩キャンパス(東京都八王子市)
    • Year and Date
      2010-09-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] 分子置換型環化付加反応による複素環新規合成法の開発2010

    • Author(s)
      倉橋拓也
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] 無水チオフタル酸とアルキンの環化付加反応によるチオイソクマリン・チオクロモン・ベンゾチオフェンの選択的合成2010

    • Author(s)
      井波輔、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] ニッケル触媒を用いたエノンとアレンの[4+2]環化付加反応2010

    • Author(s)
      酒向沙織、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] ニッケル触媒を用いたヘテロジエンとアルキンの環化付加反応による複素環合成2010

    • Author(s)
      小澤卓也、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] 脱ニトリルを伴った[4+2]環化付加反応と炭素.水素結合活性化によるアルキン付加反応を利用したビニル基置換クロモンの合成2010

    • Author(s)
      中井健一朗、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] ニッケル触媒による脱カルボニルを伴ったフタルイミドと1,3-ジエンの環化付加反応2010

    • Author(s)
      藤原恭平、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] 脱カルボニルを伴った無水フタル酸と1,2-ジエンの位置・立体選択的環化付加反応2010

    • Author(s)
      〓洋輔、倉橋拓也、松原誠二郎
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      2010-03-26
    • Related Report
      2010 Final Research Report
  • [Presentation] 分子置換型環化付加反応による複素環新規合成法の開発2010

    • Author(s)
      倉橋拓也
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] Nickel-Catalyzed Intermolecular Codimerization of Acrylamides and Alkynes.2009

    • Author(s)
      倉橋拓也、松原誠二郎
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学今出川キャンパス
    • Year and Date
      2009-09-09
    • Related Report
      2010 Final Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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