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Development of synthetic method for constructing benzo-annulated framework by utilizing arynes

Research Project

Project/Area Number 22685021
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Organic industrial materials
Research InstitutionHiroshima University

Principal Investigator

YOSHIDA Hiroto  広島大学, 大学院・工学研究院, 准教授 (40335708)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥23,140,000 (Direct Cost: ¥17,800,000、Indirect Cost: ¥5,340,000)
Fiscal Year 2012: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2011: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2010: ¥11,700,000 (Direct Cost: ¥9,000,000、Indirect Cost: ¥2,700,000)
Keywordsアライン / 芳香族縮合環骨格
Research Abstract

New method for synthesizing benzo-annulated heterocycles such as coumarins and acridanes based on the highly electrophilic character of arynes has been developed. The key intermediates in these reactions are ortho-quinoid species (ortho-quinone methide, ortho-azaxylylene) arising from formal [2+2] cycloaddition between arynes and carbon-heteroatom double bonds (dimethylformamide, imine). Subsequent [4+2] cycloaddition between the resulting ortho-quinoid species and ester enolates or second arynes provides the final products.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (9 results)

All 2012 2011 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (4 results) Remarks (1 results)

  • [Journal Article] Aryne Insertion Reactions into Carbon-Carbonδ-Bonds2012

    • Author(s)
      Hiroto Yoshida, Ken Takaki
    • Journal Title

      Synlett

      Volume: 23 Pages: 1725-1732

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Multicomponent Coupling Reaction of Arynes for Construction of Heterocyclic Skeletons2012

    • Author(s)
      Hiroto Yoshida, Ken Takaki
    • Journal Title

      Heterocycles

      Volume: 85 Pages: 1333-1349

    • NAID

      40019281393

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Three-component Coupling UsingArynes and DMF: Straightforward Access to Coumarins via ortho-Quinone Methides2011

    • Author(s)
      Hiroto Yoshida, Yu Ito, Joji Ohshita
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 8512-8514

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Three-component coupling using arynes and DMF : straightforward access to coumarins via ortho-quinone methides2011

    • Author(s)
      吉田拡人, 伊藤優, 大下浄治
    • Journal Title

      Chem.Commun.

      Volume: 47 Issue: 30 Pages: 8512-8514

    • DOI

      10.1039/c1cc11955a

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] アラインとDMF を用いた三成分連結反応:オルトキノンメチドを経由するクマリン合成2012

    • Author(s)
      吉田拡人,伊藤優,高木謙
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜市
    • Year and Date
      2012-03-25
    • Related Report
      2012 Final Research Report
  • [Presentation] アラインとDMFを用いた三成分連結反応:オルトキノンメチドを経由するクマリン合成2012

    • Author(s)
      古田拡人, 伊藤優, 高木謙
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜市
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] 芳香族化合物の合成化学2011

    • Author(s)
      吉田拡人
    • Organizer
      第43回構造有機若手の会
    • Place of Presentation
      広島県竹原市
    • Year and Date
      2011-08-03
    • Related Report
      2012 Final Research Report
  • [Presentation] 芳香族化合物の合成化学2011

    • Author(s)
      古田拡人
    • Organizer
      第43回構造有機若手の会
    • Place of Presentation
      広島県竹原市(招待講演)
    • Year and Date
      2011-08-03
    • Related Report
      2011 Annual Research Report
  • [Remarks] ホームページ

    • URL

      http://home.hiroshima-u.ac.jp/ktlab/Top/Top.html

    • Related Report
      2012 Final Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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