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Development of Synthetic Methods for Heterocycles Using Transition-Metal Catalyzed C-H Functionalization

Research Project

Project/Area Number 25460002
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMukogawa Women's University (2014-2015)
Tohoku University (2013)

Principal Investigator

INAMOTO KIYOFUMI  武庫川女子大学, 薬学部, 准教授 (30359533)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords触媒・化学プロセス / 有機化学 / 遷移金属 / C-H 官能基化 / 複素環化合物 / パラジウム / C-H官能基化 / 閉環反応 / キサンチン類 / C-H 官能基化 / 非対称化 / 炭素-水素結合官能基化 / ルテニウム / 一酸化炭素 / ジベンゾピラノン環
Outline of Final Research Achievements

Catalytic carbonylative C-H cyclization of 2-arylphenols can be achieved in the presence of a ruthenium-based catalytic system. The process proceeds efficiently under balloon pressure of CO and produces variously substituted 6H-dibenzo[b,d]pyran-6-one compounds, typically in good to high yields. In addition, a novel synthetic procedure for the construction of the xanthine framework has been developed by using a copper catalyst. Furthermore, enantioselective C-H cyclization via desymmetrization was also examined. However, the product obtained was a mixture of racemic compounds.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (28 results)

All 2016 2015 2014 2013

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Acknowledgement Compliant: 5 results,  Open Access: 1 results) Presentation (15 results) (of which Invited: 1 results) Book (1 results)

  • [Journal Article] Unusual, Chemoselective Etherification of 2-Hydroxy-1,4-naphthoquinone Derivatives Utilizing Alkoxymethyl Chlorides: Scope, Mechanism and Application to the Synthesis of Biologically Active Natural Product (±)-Lantalucratin C2016

    • Author(s)
      Tokutaro Ogata, Tomoyo Yoshida, Maki Shimizu, Manami Tanaka, Chie Fukuhara, Junko Ishii, Arisa Nishiuchi, Kiyofumi Inamoto, Tetsutaro Kimachi
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 11 Pages: 1423-1432

    • DOI

      10.1016/j.tet.2016.01.040

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Cyclization of 2-Ethynylanilines in the Presence of Isocyanates: Approach toward Indole-3-carboxamides2016

    • Author(s)
      Akiho Mizukami, Yumi Ise, Tetsutaro Kimachi, Kiyofumi Inamoto
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 4 Pages: 748-751

    • DOI

      10.1021/acs.orglett.6b00007

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] The First Enantioselective Total Synthesis of Lantalucratin C and Determination of Its Absolute Configuration2015

    • Author(s)
      Tokutaro Ogata, Manami Tanaka, Momoe Ishigaki, Maki Shimizu, Arisa Nishiuchi, Kiyofumi Inamoto, Tetsutaro Kimachi
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 38 Pages: 6672-6680

    • DOI

      10.1016/j.tet.2015.07.050

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Unusual <i>O</i>-Alkylation of 2-Hydroxy-1,4-naphthoquinone Utilizing Alkoxymethyl Chlorides2015

    • Author(s)
      Tokutaro Ogata, Tomoyo Yoshida, Manami Tanaka, Chie Fukuhara, Maki Shimizu, Junko Ishii, Arisa Nishiuchi, Kiyofumi Inamoto, Tetsutaro Kimachi
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 63 Issue: 7 Pages: 485-488

    • DOI

      10.1248/cpb.c15-00220

    • NAID

      130005085947

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Use of tetramehylammonium fluoride (TMAF) and alkali metal alkoxides as an activator for catalytic deprotonative functionalization of heteroaromatic C(sp2)-H2014

    • Author(s)
      Inamoto, Kiyofumi; Okawa, Hitomi; Kikkawa, Shoko; Kondo, Yoshinori,
    • Journal Title

      Tetrahedron

      Volume: 70 Issue: 43 Pages: 7917-7922

    • DOI

      10.1016/j.tet.2014.08.054

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hg<sup>2+</sup>-Trapping Beads: Hg<sup>2+</sup>-Specific Recognition through Thymine–Hg(II)–Thymine Base Pairing2014

    • Author(s)
      栗山光博、他12名
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 62 Issue: 7 Pages: 709-712

    • DOI

      10.1248/cpb.c13-00918

    • NAID

      130004053812

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Direct condensation of functionalized sp3 carbons with formamides for enamine synthesis using an in situ generated HMDS amide catalyst2014

    • Author(s)
      Taneda, Hiroshi; Inamoto, Kiyofumi; Kondo, Yoshinori
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 49 Pages: 6523-6525

    • DOI

      10.1039/c4cc02228a

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Desilylative carboxylation of aryltrimethylsilanes using CO2 in the presence of catalytic phosphazenium salt2014

    • Author(s)
      Yonemoto-Kobayashi, Misato; Inamoto, Kiyofumi, Kondo, Yoshinori
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 4 Pages: 477-479

    • DOI

      10.1246/cl.131108

    • NAID

      130004868067

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ruthenium-Catalyzed Carbonylative C-H Cyclization of 2-Arylphenols: A Novel Synthetic Route to 6H-Dibenzo[b,d]pyran-6-one2013

    • Author(s)
      Kiyofumi Inamoto, Jun Kadokawa, Yoshinori Kondo
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 15 Pages: 3962-3965

    • DOI

      10.1021/ol401734m

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic functionalization of heteroaromatic N-oxides with C-nucleophiles using in situ generated onium amide bases2013

    • Author(s)
      Kiyofumi Inamoto, Yuta Araki, Shoko Kikkawa, Misato Yonemoto, Yoshiyuki Tanaka, Yoshinori Kondo
    • Journal Title

      Organic &Biomolecular Chemistry

      Volume: 11 Issue: 27 Pages: 4438-4441

    • DOI

      10.1039/c3ob40782a

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system2013

    • Author(s)
      Kiyofumi Inamoto, Tetsuya Yamada, Sei-ichi Kato, Shoko Kikkawa, Yoshinori Kondo
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 44 Pages: 9192-9199

    • DOI

      10.1016/j.tet.2013.08.061

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Heterocyclic Compounds through Palladium-Catalyzed C–H Cyclization Processes2013

    • Author(s)
      Kiyofumi Inamoto
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 61 Issue: 10 Pages: 987-996

    • DOI

      10.1248/cpb.c13-00420

    • NAID

      130004137253

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 銅触媒を用いた分子内 C-H アミノ化による新規キサンチン骨格構築法の開発2016

    • Author(s)
      清水 麻希
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 抗腫瘍活性天然化合物 Rhinacanthins O、P 側鎖の合成研究2016

    • Author(s)
      西内 亜理沙
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] ロジウム触媒を用いた 2-エチニルアニリン誘導体閉環によるインドール-3-カルボキサミド類の合成2016

    • Author(s)
      稲本 浄文
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 含ハロゲンフェネチルアミンの Pd 触媒 C(sp2)-H 結合選択的アミノカルボニル化2015

    • Author(s)
      種田 宏
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      早稲田大学国際会議場(東京都新宿区)
    • Year and Date
      2015-11-19
    • Related Report
      2015 Annual Research Report
  • [Presentation] 不斉アザマイケル-フッ素化連続反応の開発研究2015

    • Author(s)
      清水 麻季
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院他(兵庫県神戸市)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] オルトナフトキノン骨格を有する抗腫瘍活性天然物 Lantalucratin C の合成研究2015

    • Author(s)
      尾形 篤太郎
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院他(兵庫県神戸市)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 抗腫瘍活性天然物 Rhinacanthins の合成研究2015

    • Author(s)
      西内 亜理紗
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院他(兵庫県神戸市)
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 活性化マクロファージの NO 産生を抑制するチオフェン-2-イルおよびチオフェン-3-イルナフトキノン類の合成2014

    • Author(s)
      尾形 篤太郎
    • Organizer
      第64回日本薬学会近畿支部総会・大会
    • Place of Presentation
      京都薬科大学(京都府京都市)
    • Year and Date
      2014-10-11
    • Related Report
      2014 Research-status Report
  • [Presentation] 不斉アミノ化を起点とする新規なフッ素導入法の開発と環状アルカロイド類合成への応用2014

    • Author(s)
      清水 麻季
    • Organizer
      第64回日本薬学会近畿支部総会・大会
    • Place of Presentation
      京都薬科大学(京都府京都市)
    • Year and Date
      2014-10-11
    • Related Report
      2014 Research-status Report
  • [Presentation] 抗腫瘍活性を有する天然物 Lantalucratin C の合成研究2014

    • Author(s)
      田中 愛美
    • Organizer
      第64回日本薬学会近畿支部総会・大会
    • Place of Presentation
      京都薬科大学(京都府京都市)
    • Year and Date
      2014-10-11
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis of 2-Quinolinones through a Tadem-Type, Pd(II)-Catalyzed Oxidative Heck Reaction/Intramolecular C-H Amidation Sequence2013

    • Author(s)
      Kiyofumi Inamoto
    • Organizer
      The 23rd French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      長崎,クラウンプラザ ANA
    • Related Report
      2013 Research-status Report
  • [Presentation] 遷移金属触媒を用いた新規プロセスの開発と,その過程で見つけた遷移金属触媒を用いない反応2013

    • Author(s)
      稲本 浄文
    • Organizer
      第12回化学系薬学若手研究者セミナー
    • Place of Presentation
      仙台,東北大学薬学研究科
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] ルテニウム触媒による C-H 閉環反応を利用した dibenzopyranone 類合成2013

    • Author(s)
      稲本 浄文
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      岐阜,長良川国際会議場
    • Related Report
      2013 Research-status Report
  • [Presentation] ルテニウム触媒 C-H カルボニル化を利用したジベンゾピラノン骨格の新規合成法の開発2013

    • Author(s)
      門川 純
    • Organizer
      第52回日本薬学会東北支部大会
    • Place of Presentation
      仙台,東北大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ルテニウム触媒 C-H カルボニル化を用いたジベンゾピラノン骨格の新規構築法の開発2013

    • Author(s)
      門川 純
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡,九州大学
    • Related Report
      2013 Research-status Report
  • [Book] Cross Coupling and Heck-Type Reactions 22013

    • Author(s)
      Kiyofumi Inamoto
    • Total Pages
      708
    • Publisher
      Thieme
    • Related Report
      2013 Research-status Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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