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2012 Fiscal Year Final Research Report

Regiocontrol of heteroaryne reactions by redox change

Research Project

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Project/Area Number 23790017
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

IKAWA Takashi  静岡県立大学, 薬学部, 助教 (20453061)

Project Period (FY) 2011 – 2012
Keywordsピリダイン / イソキノリン / Diels-Alder 反応 / 位置選択性 / ケイ素官能基 / フラン / 複素環 / カップリング
Research Abstract

A new synthetic route to isoquinoline derivatives consisting regioselective Diels-Alder reactions of 3,4-pyridynes with furans and following functional group transformations is reported. The key for the regioselectivity of the cycloaddition reactions is electropositive silicon atom of the 2-position of 3,4-pyridyne. This directing group can also be substituted with various functional groups.

  • Research Products

    (18 results)

All 2013 2012 2011 2010

All Journal Article (8 results) Presentation (10 results)

  • [Journal Article] Generation of 3-Borylbenzynes, Their Regioselective Diels-Alder Reactions, and Theoretical Analysis2013

    • Author(s)
      Takagi Akira, Ikawa Takashi, Kurita Yurio, Saito Kozumo, Azechi Kenji, Egi Masahiro, Itoh Yuji, Tokiwa Hiroaki, Kita Yasuyuki, Akai Shuji
    • Journal Title

      Tetrahedron

      Volume: 69 Pages: 4338-4352

    • DOI

      DOI: 10.1016/j.tet.2013.03.016

  • [Journal Article] Regiocomplementary Cycloaddition Reactions of Boryl- and Silylbenzynes with 1,3-Dipoles: Selective Synthesis of Benzo-Fused Azole Derivatives2013

    • Author(s)
      Ikawa Takashi, Takagi Akira, Goto Masahiko, Aoyama Yuya, Ishikawa Yoshinobu, Itoh Yuji, Fujii Satoshi, Tokiwa Hiroaki, Akai Shuji
    • Journal Title

      J. Org. Chem.

      Volume: 78 Pages: 2965-2983

    • DOI

      DOI: 10.1021/jo302802b

  • [Journal Article] Discovery of Aromatic Components with Excellent Fragrance Properties and Biological Activities: β-Ionols with Antimelanogenetic Effects and Their Asymmetric Syntheses2013

    • Author(s)
      Komaki Ryoichi, Ikawa Takashi, Saito Kozumo, Hattori Kazuyo, Ishikawa Natsuyo, Fukawa Hidemichi, Egi Masahiro, Akai Shuji
    • Journal Title

      Chem. Pharm. Bull.

      Volume: 61 Pages: 310-314

    • DOI

      DOI: 10.1248/cpb.c12-00916

  • [Journal Article] Palladium-Catalyzed One-Pot Cross-Coupling of Phenols Using Nonafluorobutanesulfonyl Fluoride2012

    • Author(s)
      Ikawa Takashi, Saito Kozumo, Akai Shuji
    • Journal Title

      Synlett

      Volume: 23 Pages: 2241-2246

    • DOI

      DOI: 10.1055/s-0032-1317076

  • [Journal Article] Selective N-Alkylation of Amines Using Nitriles under Hydrogenation Conditions: Facile Synthesis of Secondary and Tertiary Amines2012

    • Author(s)
      Ikawa Takashi, Fujita Yuki, Mizusaki Tomoteru, Betsuin Sae, Takamatsu Haruki, Maegawa Tomohiro, Monguchi Yasunari, Sajiki Hironao
    • Journal Title

      Org. Biomol. Chem.

      Volume: 10 Pages: 293-304

    • DOI

      DOI: 10.1039/C1OB06303K

  • [Journal Article] ortho-Selective Nucleophilic Addition of Primary Amines to Silylbenzynes: Synthesis of 2-Silylanilines2011

    • Author(s)
      Ikawa Takashi, Nishiyama Tsuyoshi, Shigeta Takashi, Mohri Shinya, Morita Shinsuke, Takayanagi Sho-ichi, Terauchi Yuki, Morikawa Yuki, Takagi Akira, Ishikawa Yoshinobu, Fujii Satoshi, Kita Yasuyuki, Akai Shuji
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 5674

    • DOI

      DOI:10.1002/anie.201100360

  • [Journal Article] A Domino Process for Benzyne Preparation: Dual Activation of o-(Trimethylsilyl)phenols by Nonafluorobutanesulfonyl Fluoride2011

    • Author(s)
      Ikawa Takashi, Nishiyama Tsuyoshi, Nosaki Toshifumi, Takagi Akira, Akai Shuji
    • Journal Title

      Org. Lett.

      Volume: 13 Pages: 1730-1733

    • DOI

      DOI: 10.1021/ol200252c

  • [Journal Article] Preparation of Borylbenzynes and Their Regioselective Diels-Alder Reaction: Synthesis of Functionalized Arylboronates2010

    • Author(s)
      Ikawa Takashi, Takagi Akira, Kurita Yurio, Saito Kozumo, Azechi Kenji, Egi Masahiro, Kakiguchi Keisuke, Kita Yasuyuki, Akai Shuji
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49 Pages: 5563-5566

    • DOI

      DOI: 10.1002/anie.201002191

  • [Presentation] Experimental and Theoretical Study on Regioselective Reactions of 3-Silyl-and 3-Borylbenzyne2013

    • Author(s)
      Ikawa Takashi, Takagi Akira, Akai Shuji
    • Organizer
      The 6th Heron Island Conference on Reactive Intermediates and Unusual Molecules: Synthesis and Mechanism (Heron 6)
    • Place of Presentation
      Australia
    • Year and Date
      20130707-13
  • [Presentation] Regioselective Diels-Alder Reactions of 2-Silyl-3,4-pyridynes with Furans: Selective Synthesis of Isoquinolines2013

    • Author(s)
      Ikawa Takashi, Urata Hirohito, Nishiyama Tsuyoshi, Akai Shuji
    • Organizer
      23nd French-Japanese Symposium of Medicinal and Fine Chemistry
    • Place of Presentation
      Nagasaki, Japan
    • Year and Date
      20130512-15
  • [Presentation] NfF-Mediated in-situ Activation of Phenols for Benzyne Generation and Coupling Reactions2012

    • Author(s)
      Ikawa Takashi, Saito Kozumo, Nishiyama Tsuyoshi, Nosaki Toshifumi, Takagi Akira, Akai Shuji
    • Organizer
      The 6th Takeda Science Foundation Symposium on PharmaSciences
    • Place of Presentation
      Osaka, Japan
    • Year and Date
      20120913-14
  • [Presentation] Regioselective Cycloaddition Reactions of Silyl-and Boryl-Benzynes: Regiocontrolled Synthesis of Multisubstituted Aromatic Compounds2012

    • Author(s)
      Takagi Akira, Ikawa Takashi, Takayanagi Sho-ichi, Goto Masahiko, Aoyama Yuya, Itoh Yuji, Tokiwa Hiroaki, Akai Shuji
    • Organizer
      The 6th Takeda Science Foundation Symposium on PharmaSciences
    • Place of Presentation
      Osaka, Japan
    • Year and Date
      20120913-14
  • [Presentation] シリル置換ピリダインの位置選択的Diels-Alder反応:多置換イソキノリンの構築2012

    • Author(s)
      浦田博一,西山剛史,井川貴詞,赤井周司
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2012-11-06
  • [Presentation] 置換ベンザインの(3+2)環化付加反応による縮合芳香族複素環の位置選択的合成2012

    • Author(s)
      高木晃,井川貴詞,後藤雅彦,青山祐也,赤井周司
    • Organizer
      第29回有機合成化学セミナー
    • Place of Presentation
      静岡
    • Year and Date
      2012-09-06
  • [Presentation] 置換基効果を用いる3,4-ピリダインの位置選択的環化付加反応2012

    • Author(s)
      井川貴詞,浦田博一,西山剛史,赤井周司
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-30
  • [Presentation] Practical Benzyne Preparation from Phenol Derivatives Using NfF2011

    • Author(s)
      Ikawa Takashi, Nishiyama Tsuyoshi, Akai Shuji
    • Organizer
      The 2nd International Symposium for Process Chemistry
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      20110810-12
  • [Presentation] Regiocontrol of Cycloaddition Reactions of Benzynes by Bory and Silyl Substituents2011

    • Author(s)
      Akai Shuji, Ikawa Takashi, Takagi Akira, Takayanagi Sho-ichi
    • Organizer
      22nd French-Japanese Symposium of Medicinal and Fine Chemistry
    • Place of Presentation
      Rouen, France
    • Year and Date
      2011-09-12
  • [Presentation] Theoretical Study of Regioselectivities in the Diels-Alder Reactions between Substituted Benzynes and Furans2011

    • Author(s)
      Takagi Akira, Ikawa Takashi, Takayanagi Sho-ichi, Itoh Yuji, Tokiwa Hiroaki, Akai Shuji
    • Organizer
      Ninth Triennial Congress of the World Association of Theoretical and Computational Chemists (WATOC) 2011
    • Place of Presentation
      Santiago de Compostela, Spain
    • Year and Date
      2011-07-19

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Published: 2014-08-29   Modified: 2014-10-09  

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