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Efficient synthesis of multifunctionalyzed heterocycles using isocyanides

Research Project

Project/Area Number 15K17820
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionKanazawa University

Principal Investigator

Soeta Takahiro  金沢大学, 物質化学系, 准教授 (10506819)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsイソシアニド / 多成分反応 / 複素環 / 触媒的不斉反応
Outline of Final Research Achievements

Isocyanide is one of the most important building blocks in the organic chemistry because isocyanide has nucleophilicity and electrophilicity on the carbon atom. We have developed [n+1] cycloaddition reaction of isocyanide with 1,n-dipolars to afford the corresponding hetecocycles in high yields.

Report

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

    (38 results)

All 2017 2016 2015

All Journal Article (13 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 12 results,  Acknowledgement Compliant: 4 results,  Open Access: 1 results) Presentation (25 results) (of which Int'l Joint Research: 2 results)

  • [Journal Article] 2.Development of a One-Pot Synthetic Method for Multifunctional Oxazole Derivatives Using Isocyanide Dichloride.2017

    • Author(s)
      Soeta, T.; Matsumoto, A.; Sakata, Y.; Ukaji, Y
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 9 Pages: 4930-4935

    • DOI

      10.1021/acs.joc.7b00296

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Formal Total Synthesis of Manzacidin C Based on Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines.2017

    • Author(s)
      Tong, T. M. T.; Soeta, T.; Suga, T.; Kawamoto, K.; Hayaahi, Y.; Ukaji, Y.
    • Journal Title

      J. Org. Chem.

      Volume: 82 Pages: 1969-1976

    • NAID

      120006027761

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Palladium-catalyzed C–H Alkenylation of <i>C</i>-Aryl Nitrones2017

    • Author(s)
      Hasegawa, M.; Nomoto, A.; Suga, T.; Soeta, T.; Ukaji, Y.
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 1 Pages: 45-47

    • DOI

      10.1246/cl.160821

    • NAID

      130005308312

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Effective synthesis of Benzothiophenes by [4+1] Cycloaddition of 2-Mercaptobenzaldehyde Derivatives with Isocyanides.2016

    • Author(s)
      Soeta, T.; Shitaya, S.; Okuno, T.; Fujinami, S.; Ukaji, Y.
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 49 Pages: 7901-7905

    • DOI

      10.1016/j.tet.2016.09.054

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Intermolecular Alkoxy-Alkoxycarbonylation of Vinylphenols in the Presence of Copper Salt: Unexpected Cooperative Effect of Tin Salt.2016

    • Author(s)
      Phan, N. H. T.; Furuya, T.; Soeta, T.; Ukaji, Y.
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 12 Pages: 1431-1433

    • DOI

      10.1246/cl.160804

    • NAID

      130005475736

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Ugi-type Multicomponent Reaction of Nitrile Imines, Isocyanides, and Isocyanates: Effective Synthesis of 1,2,4-Triazinedione Derivatives.2016

    • Author(s)
      Soeta, T.; Takashita, S.; Sakata, Y.; Ukaji, Y.
    • Journal Title

      Asian J. Org. Chem.

      Volume: 5 Issue: 8 Pages: 1041-1047

    • DOI

      10.1002/ajoc.201600191

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] 8.Magnesium-Alkoxide Directed Photoaddition of Tetrahydrofyrans to γ,γ-Disubstituted Allylic Alcohols.2016

    • Author(s)
      Watanabe, Y.; Sakai, T.; Maeda, H.; Segi, M.; Soeta, T.; Ukaji, Y
    • Journal Title

      Heterocycles

      Volume: 93 Issue: 2 Pages: 833-844

    • DOI

      10.3987/com-15-s(t)65

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Pre-steady-state Kinetic Studies of Redox Reactions Catalysed by Bacillus Subtilis Ferredoxin-NADP+ Oxidoreductase with NADP+/NADPH and Ferredoxin.2016

    • Author(s)
      Seo, D.; Soeta, T.; Sakurai, H.; Pierre, S.; Sakurai, T.
    • Journal Title

      BBA-BIOENERGETICS

      Volume: 1 Pages: 309-311

    • NAID

      120005774908

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-Tosylaldimines2016

    • Author(s)
      Soeta, T.; Ishizaka, T.; Ukaji, Y.
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 7 Pages: 2817-2826

    • DOI

      10.1021/acs.joc.6b00093

    • Related Report
      2015 Research-status Report
  • [Journal Article] Phosphinic Acid-promoted Addition Reaction of Isocyanides to (Z)-Hydroximoyl Chlorides: Efficient Synthesis of α-(Hydroxyimino)amides.2015

    • Author(s)
      Soeta, T. Takashita, S.; Sakata, Y.; Ukaji, Y.
    • Journal Title

      Org. Biomol.Chem.

      Volume: 14 Issue: 2 Pages: 694-700

    • DOI

      10.1039/c5ob02032h

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] A One-Pot O-Sulfinative Passerini/Oxidation Reaction: Efficient Synthesis of α-(Sulfonyloxy)amide Derivatives.2015

    • Author(s)
      Soeta, T.; Matsuzaki, S.; Ukaji, Y.
    • Journal Title

      J. Org. Chem

      Volume: 80 Issue: 7 Pages: 3688-3694

    • DOI

      10.1021/acs.joc.5b00131

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-Carbon Homologation of Pyrrole Carboxaldehyde via Wittig Reaction and Mild Hydrolysis of Vinyl Ether &#8211; toward the Synthesis of a Sterically Locked Phytochrome Chromophore.2015

    • Author(s)
      Sakata, R.; Soeta, T.; Ukaji, Y.
    • Journal Title

      Heterocycles

      Volume: 91 Pages: 593-603

    • NAID

      40020393284

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] (Z)-Selective Enol Triflation of α-Alkoxyacetoaldehydes: Application to Synthesis of (Z)-Allylic Alcohols via Cross-Coupling Reaction and [1,2]-Wittig Rearrangement2015

    • Author(s)
      Kurosawa, F.; Nakano, T.; Soeta, T.; Endo, K.; Ukaji, Y.
    • Journal Title

      J. Org. Chem.

      Volume: 80 Issue: 11 Pages: 5696-5603

    • DOI

      10.1021/acs.joc.5b00647

    • NAID

      120005647656

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] メソ位立体固定型フィトクロム発色団の開発とその光異性化の機構解明2017

    • Author(s)
      大橋 信彦・小林 俊晴・添田 貴宏・宇梶 裕
    • Organizer
      日本化学会 第97春季年会 (2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ピリジン骨格を有するキラルな含窒素複素環カルベンを用いる触媒的不斉クロスベンゾイン縮合の開発2017

    • Author(s)
      水野 想・添田 貴宏・宇梶 裕
    • Organizer
      日本化学会 第97春季年会 (2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] α,β-不飽和ニトロンを用いたイリドとの反応によるジヒドロ オキサジン誘導体の合成2017

    • Author(s)
      長谷川恵美・菅 拓也・ 添田貴宏・宇梶 裕
    • Organizer
      日本化学会 第97春季年会 (2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Enantioselective Synthesis of γ-Lactams via Palladium-Catalyzed Carbonylation of Homoallylic Amine Derivatives2017

    • Author(s)
      PHAN, Nga Hang Thi; SUGA, Takuya; SOETA, Takahiro; UKAJI, Yutaka
    • Organizer
      日本化学会 第97春季年会 (2017)
    • Place of Presentation
      慶應義塾大学 日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Formal Total Synthesis of Manzacidin C via Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imine2016

    • Author(s)
      Tong Thi Minh Thu, Takahiro Soeta, Yutaka Ukaji
    • Organizer
      平成28年度有機合成化学北陸セミナー
    • Place of Presentation
      石川県青少年センター
    • Year and Date
      2016-10-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] 下矢沙央里・奥野 巧・添田貴宏・宇梶 裕2016

    • Author(s)
      イソシアニドを用いた[4+1]付加環化反応の開発: ベンゾチオフェン誘導体の高効率的合成
    • Organizer
      平成28年度有機合成化学北陸セミナー
    • Place of Presentation
      石川県青少年センター
    • Year and Date
      2016-10-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] ピリジン骨格を有するキラルな含窒素複素環カルベンを用いた 触媒的不斉クロスベンゾイン縮合の開発2016

    • Author(s)
      水野 想・添田貴宏・宇梶 裕
    • Organizer
      平成28年度有機合成化学北陸セミナー
    • Place of Presentation
      石川県青少年センター
    • Year and Date
      2016-10-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] Palladium-Catalyzed Intermolecular Alkoxy-Alkoxycarbonylation of Vinylphenols2016

    • Author(s)
      Phan Thi Hang Nga・Tomoki Furuya・ Takahiro Soeta・Yutaka Ukaji
    • Organizer
      平成28年度有機合成化学北陸セミナー
    • Place of Presentation
      石川県青少年センター
    • Year and Date
      2016-10-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] 1,3-双極子を鍵とする新規Ugi型反応の開発2016

    • Author(s)
      添田貴宏・高下 卓・宮本祥明・宇梶 裕
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢市歌劇座
    • Year and Date
      2016-09-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] イソシアニドジクロリドを鍵中間体とした 多官能性ジヒドロオキサゾール誘導体の新規One-Pot合成2016

    • Author(s)
      松本 昂大・添田 貴宏・宇梶 裕
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢市歌劇座
    • Year and Date
      2016-09-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] ニトロンを配向基としたパラジウム触媒によるC-H活性化反応の開発2016

    • Author(s)
      長谷川恵美・野本有紗・ 添田貴宏・宇梶 裕
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢市歌劇座
    • Year and Date
      2016-09-26
    • Related Report
      2016 Annual Research Report
  • [Presentation] イソシアニドを用いた[4+1]付加環化反応の開発: ベンゾチオフェン誘導体の高効率的合成2016

    • Author(s)
      下矢沙央里,奥野 巧,添田貴宏,宇梶 裕
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] イソシアネートを活用した新規Ugi型反応の開発:高効率的1,2,4-トリアジノン誘導体の合成2016

    • Author(s)
      高下 卓・添田貴宏・宇梶 裕
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines Utilizing Tartaric Acid Ester as a Chiral Auxiliary2016

    • Author(s)
      Tong Thi Minh Thu, Takahiro Soeta, Yutaka Ukaji
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Carboxylic Acid Free Novel Isocyanide-Based Reactions2015

    • Author(s)
      Takahiro Soeta
    • Organizer
      pacifichem2015
    • Place of Presentation
      ハワイ,ホノルル
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines Utilizing Tartaric Acid Ester as a Chiral Auxiliary2015

    • Author(s)
      Tong Thi Minh Thu, Takahiro Soeta, Yutaka Ukaji
    • Organizer
      日本化学会近畿支部平成27年度北陸地区講演会と研究発表会
    • Place of Presentation
      金沢大学
    • Year and Date
      2015-11-27
    • Related Report
      2015 Research-status Report
  • [Presentation] 多点認識型 NHC 配位子を用いたN-スルホニルイミンへの 触媒的不斉アルキル化反応2015

    • Author(s)
      石坂智洋・添田貴宏・宇梶 裕
    • Organizer
      日本化学会近畿支部平成27年度北陸地区講演会と研究発表会
    • Place of Presentation
      金沢大学
    • Year and Date
      2015-11-27
    • Related Report
      2015 Research-status Report
  • [Presentation] ホスフィン酸を活性化剤とした新規Ugi型反応の開発2015

    • Author(s)
      高下 卓・添田貴宏・宇梶 裕
    • Organizer
      日本化学会近畿支部平成27年度北陸地区講演会と研究発表会
    • Place of Presentation
      金沢大学
    • Year and Date
      2015-11-27
    • Related Report
      2015 Research-status Report
  • [Presentation] アリルアルコールへのテトラヒドロフラン類の位置選択的光付加反応2015

    • Author(s)
      渡邊康貴・坂井飛大・前多 肇・千木昌人・添田貴宏・宇梶 裕
    • Organizer
      平成27年度有機合成化学北陸セミナー
    • Place of Presentation
      金沢大学
    • Year and Date
      2015-11-27
    • Related Report
      2015 Research-status Report
  • [Presentation] 多点認識型NHC配位子を用いた N-スルホニルイミンへの触媒的不斉アルキル化反応2015

    • Author(s)
      石坂 智洋・添田 貴宏・宇梶 裕
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      早稲田大学
    • Year and Date
      2015-11-19
    • Related Report
      2015 Research-status Report
  • [Presentation] Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines Utilizing Tartaric Acid Ester as a Chiral Auxiliary2015

    • Author(s)
      Tong Thi Minh Thu, Takahiro Soeta, Yutaka Ukaji
    • Organizer
      The Thirteenth International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto
    • Year and Date
      2015-11-09
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines Utilizing Tartaric Acid Ester as a Chiral Auxiliary2015

    • Author(s)
      Tong Thi Minh Thu・添田貴宏・宇梶 裕
    • Organizer
      平成27年度有機合成化学北陸セミナー
    • Place of Presentation
      富山
    • Year and Date
      2015-10-02
    • Related Report
      2015 Research-status Report
  • [Presentation] 多点認識型NHC配位子を用いたN-スルホニルイミンへの 触媒的不斉アルキル化2015

    • Author(s)
      石坂智洋・添田貴宏・宇梶 裕
    • Organizer
      平成27年度有機合成化学北陸セミナー
    • Place of Presentation
      富山
    • Year and Date
      2015-10-02
    • Related Report
      2015 Research-status Report
  • [Presentation] ホスフィン酸を活性化剤とした新規Ugi型反応の開発2015

    • Author(s)
      高下 卓・添田貴宏・宇梶 裕
    • Organizer
      平成27年度有機合成化学北陸セミナー
    • Place of Presentation
      富山
    • Year and Date
      2015-10-02
    • Related Report
      2015 Research-status Report
  • [Presentation] アリルアルコールへのテトラヒドロフラン類の位置選択的光付加反応2015

    • Author(s)
      渡邊康貴・坂井飛大・前多 肇・千木昌人・添田貴宏・宇梶 裕
    • Organizer
      平成27年度有機合成化学北陸セミナー
    • Place of Presentation
      富山
    • Year and Date
      2015-10-02
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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