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Synthesis of poly-substituted aromatic compounds from diazonaphthoquinone

Research Project

Project/Area Number 26410054
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionKyushu Institute of Technology

Principal Investigator

Kitamura Mitsuru  九州工業大学, 大学院工学研究院, 教授 (10313199)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsdiazonaphthoquinones / diazo compounds / Rh / Pd / carbene / ジアゾキノン / ジアゾ化合物 / ナフトフラン / クロスカップリング / ジアゾナフトキノン / ベンゾナフトピラノン / ジアゾ移動反応 / グアニジノジアゾニウム塩
Outline of Final Research Achievements

The diazo-transfer reactions of 2-azido-1,3-dimethylimidazolinium chlorides (ADMC) to naphthols proceeded smoothly to give corresponding diazonaphthoquinones in high yields. We developed several synthetic methods of poly-substituted arenes by metal-catalyzed reaction of diazonaphthoquinones. 3-Aryloxycarbonyldiazonaphthoquinones were transformed to β-phenylnaphthalene lactones through Rh-catalyzed intramolecular formal C-H insertion reaction. This lactone formation was efficiently applied to the formal total synthesis of pradimicinone. Naphthofurans were selectivity synthesized from diaozonaphthoquinones and terminal alkynes catalyzed by Cu and Pd reagents.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (21 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (1 results) Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results,  Acknowledgement Compliant: 3 results) Presentation (12 results) (of which Invited: 1 results)

  • [Int'l Joint Research] マンソウラ大学(エジプト)

    • Related Report
      2016 Annual Research Report
  • [Journal Article] Synthesis of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP)2016

    • Author(s)
      M. Kitamura, K. Murakami
    • Journal Title

      Organic Syntheses

      Volume: 92 Pages: 171-181

    • DOI

      10.15227/orgsyn.092.0171

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Axially Chiral Bifunctional 8,8′-Biquinolyl: Synthesis of 7,7′-Dihydroxymethyl-8,8′-biquinolyl via Pd-Catalyzed Double C-H Oxidation of 7,7′-Dimethyl-8,8′-biquinolyl2016

    • Author(s)
      M. Kitamura, H. Fukuma, M. Kobayashi, S. Okayama, T. Okauchi
    • Journal Title

      Journal of Organic Chemistry

      Volume: 81 Issue: 9 Pages: 3956-3960

    • DOI

      10.1021/acs.joc.6b00534

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, structure, and reaction of chiral 2-azidoimidazolinium salts: (7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate2016

    • Author(s)
      M. Kitamura, A. Ishikawa, T. Okauchi
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 16 Pages: 1794-1797

    • DOI

      10.1016/j.tetlet.2016.03.036

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Diazonaphthoquinones: Synthesis, reactions and applications2016

    • Author(s)
      D.I.A Othman, M. Kitamura
    • Journal Title

      Heterocycles

      Volume: 92 Issue: 10 Pages: 1761-1783

    • DOI

      10.3987/rev-16-845

    • NAID

      40020980890

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Rh-Catalyzed Cyclization of 3‐Aryloxycarbonyldiazonaphthoquinones for the Synthesis of β‐Phenylnaphthalene Lactones and Formal Synthesis of Pradimicinone2015

    • Author(s)
      Mitsuru Kitamura, Shuhei Takahashi, Tatsuo Okauchi
    • Journal Title

      J. Org. Chem.

      Volume: 80 Issue: 16 Pages: 8406-8416

    • DOI

      10.1021/acs.joc.5b01251

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Diazonaphthoquinones from Naphthols by Diazo-Transfer Reaction2015

    • Author(s)
      Kitamura, M.; Sakata, R.; Tashiro, N.; Ikegami, A.; Okauchi, T.
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 88 Issue: 6 Pages: 824-833

    • DOI

      10.1246/bcsj.20150021

    • NAID

      130005075682

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Pd(OAc)2-Catalyzed Macrocyclization of 1,2-Diazonaphthoquinones with Cyclic Ethers2014

    • Author(s)
      Kitamura, M.; Kisanuki, M.; Kanemura, K.; Okauchi, T.
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 6 Pages: 1554-1557

    • DOI

      10.1021/ol500222s

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthetic study of kosinostatin aglycone: Synthesis of BCDE rings using alkoxycarbonylmethylation of diazonaphthoquinone2014

    • Author(s)
      Kitamura, M.; Kubo, K.; Yoshinaga, S.; Matsuzaki, H.; Ezaki, K.; Matsuura, T.; Matsuura, D.; Fukuzumi, N.; Araki, K.; Narasaki, M.
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Issue: 23 Pages: 1653-1656

    • DOI

      10.1016/j.tetlet.2014.10.140

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] d触媒を用いたジアゾナフトキノンとアルキンの反応によるナフトフランの合成2017

    • Author(s)
      髙橋 周平, 岡内 辰夫, 北村 充
    • Organizer
      日本化学会第97回春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Pd触媒を用いたジアゾナフトキノンとアルキン類からのナフトフラン合成2016

    • Author(s)
      髙橋 周平, 岡内 辰夫, 北村 充
    • Organizer
      第53回化学関連支部合同九州大会
    • Place of Presentation
      金沢
    • Year and Date
      2016-09-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] ロジウム触媒を用いた 3-アルコキシ-1,2-ジアゾナフトキノンの C-H/O-H 挿入反応2016

    • Author(s)
      大塚孔太,高橋周平,岡内辰夫,北村 充
    • Organizer
      日本化学会 第96春季年会 (2016)
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] パラジウム触媒を用いたジアゾナフトキノンとアルキニルスズ とのカップリング反応2016

    • Author(s)
      髙橋周平,岡内 辰夫,北村 充
    • Organizer
      日本化学会 第96春季年会 (2016)
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ロジウム触媒を用いたジアゾナフトキノンからのベンゾナフトピラノンの合成2016

    • Author(s)
      髙橋 周平, 岡内 辰夫, 北村 充
    • Organizer
      第26回万有福岡シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2016 Annual Research Report
  • [Presentation] Pd触媒を用いたジアゾナフトキノンとアルキン類とのカップリング反応2016

    • Author(s)
      髙橋 周平, 岡内 辰夫, 北村 充
    • Organizer
      第53回化学関連支部合同九州大会
    • Place of Presentation
      北九州
    • Related Report
      2016 Annual Research Report
  • [Presentation] ジアゾキノンを用いるコシノスタチンアグリコンの合成研究2015

    • Author(s)
      清水 湧太郎,福住 謙亨,北村 充
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      早稲田大学
    • Year and Date
      2015-11-21
    • Related Report
      2015 Research-status Report
  • [Presentation] ロジウム触媒を用いたジアゾナフトキノンからのベンゾナフトピラノンの合成2015

    • Author(s)
      髙橋周平,岡内 辰夫,北村 充
    • Organizer
      第52回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Research-status Report
  • [Presentation] 分子内C-H結合挿入反応を利用したジアゾナフトキノンからのナフトフラノン骨格の構築2015

    • Author(s)
      大塚孔太,高橋周平,岡内辰夫,北村 充
    • Organizer
      第52回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Research-status Report
  • [Presentation] コシノスタチンアグリコンの合成研究2015

    • Author(s)
      清水 湧太郎,岡内 辰夫,北村 充
    • Organizer
      第52回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Research-status Report
  • [Presentation] ロジウム触媒を用いたジアゾナフトキノンからのベンゾナフトピラノンの合成2015

    • Author(s)
      髙橋 周平・兼村 晃一・岡内 辰夫・北村 充
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Safe and Efficient Diazo-transfer Reagents: 2-Azido-1,3-dimethylimidazolinium Salts2014

    • Author(s)
      M. Kitamura, N. Tashiro, R. Sakata, S. Miyagawa, M. Yano, K. Murakami, S. Kato
    • Organizer
      8th Singapore International Chemistry Conference 2014
    • Place of Presentation
      シンガポール
    • Year and Date
      2014-12-14 – 2014-12-17
    • Related Report
      2014 Research-status Report
    • Invited

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Published: 2014-04-04   Modified: 2018-03-22  

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