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Development of novel isocyanide-based reactions

Research Project

Project/Area Number 24750037
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, 助教 (10506819)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywords多成分反応 / イソシアニド / 複素環 / 含窒素複素環
Research Abstract

In order to develop a practical method for the construction of crud like and heterocyclic compounds, we have designed a novel Passerini or Ugi reaction system where a compound (which we write in the general form as Z-X) composed of an electrophilic (Z) and nucleophilic (X) could perform the same reactivity as the carboxylic acid. Based on this concept, we have developed the O-silylative Passerini reaction and the borinic acid catalyzed addition of isocyanides to aldehydes. In addition, we have designed and demonstrated the addition reaction of isocyanides to nitrones in the presence of silly halide. Furthermore, a novel [5+1] cycloaddition of isocyanide was explored to afford the hetelocyclic compounds efficiency.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (43 results)

All 2014 2013 2012

All Journal Article (17 results) (of which Peer Reviewed: 17 results) Presentation (24 results) Book (2 results)

  • [Journal Article] [4+1] Cycloaddition of N-Acyl Imine Derivatives with Isocyanides: Efficient Synthesis of 5-Aminooxazoles and 5-Aminothiazoles.2014

    • Author(s)
      T. Soeta, K. Tamura, Y. Ukaji
    • Journal Title

      Tetrhedron

      Volume: 70 Issue: 18 Pages: 3005-3010

    • DOI

      10.1016/j.tet.2014.03.016

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] A One-Pot O-Phosphinative Passerini/Pudovik Reaction: Efficient Synthesis of Highly Functionalized α-(Phosphinyloxy)amide Derivatives.2014

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

      Chem. -Eur. J.

      Volume: 20 Issue: 17 Pages: 5007-5012

    • DOI

      10.1002/chem.201304618

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Desymmetrization of 1,4-Pentadien-3-ol by the Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines2014

    • Author(s)
      M. Yoshida, N. Sassa, T. Kato, S. Fujinami, T. Soeta, K. Inomata, Y. Ukaji
    • Journal Title

      Chem. -Eur. J.

      Volume: 20 Issue: 7 Pages: 2058-2064

    • DOI

      10.1002/chem.201302889

    • NAID

      120005368204

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Carboxylic Acid-Free Novel Isocyanide Based Reactions2014

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

      Chem. Rec.

      Volume: 14 Issue: 1 Pages: 101-116

    • DOI

      10.1002/tcr.201300021

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of (2Z,4E)-2,4-Pentadien-1-ols via Sequential 1,4-Elimination Reaction and [1,2]-Wittig Rearrangement Starting from (E)-4-Alkoxy-2-butenyl Benzoates.2013

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

      J. Org. Chem.

      Volume: 78 Issue: 24 Pages: 12654-12661

    • DOI

      10.1021/jo402272r

    • NAID

      120005368203

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Magnesium-Tartramide Complex Mediated Asymmetric Strecker-Type Reaction of Nitrones Using Cyanohydrin.2013

    • Author(s)
      T. Sakai, T. Soeta, K. Endo, S. Fujinami, Y. Ukaji
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 10 Pages: 2422-2425

    • DOI

      10.1021/ol400898p

    • NAID

      120005254078

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with Carbodiimides under Aerobic Conditions: Efficient Synthesis of N-Acylureas.2013

    • Author(s)
      T. Soeta, Y. Tabatake, S. Fujinami, Y. Ukaji
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 9 Pages: 2088-2091

    • DOI

      10.1021/ol400672c

    • Related Report
      2013 Annual Research Report 2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Three-Component Reaction of C, N-Cyclic N'-Acyl Azomethine Imine, Isocyanide, and Azide Compounds : Effective Synthesis of 1,5-Disubstituted Tetrazoles with Tetrahydroisoquinoline Skeletons2013

    • Author(s)
      T. Soeta
    • Journal Title

      Org. Biomol. Chem.

      Volume: 11 Issue: 13 Pages: 2168-2174

    • DOI

      10.1039/c3ob27297d

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-pot Stereoselective Syntheses of 2-Acylaziridines and 2-Acylpyrrolidines from N-(Propargylic)hydroxylamines2013

    • Author(s)
      Y. Miyamoto
    • Journal Title

      Chem, -Asian J

      Volume: 8 Issue: 4 Pages: 824-831

    • DOI

      10.1002/asia.201201180

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] The Chlorosilane-Promoted Addition Reaction of Isocyanides to 3,4-Dihydroisoquinoline N-Oxides2012

    • Author(s)
      T. Soeta
    • Journal Title

      J.Org.Chem.

      Volume: 77 Issue: 21 Pages: 9878-9883

    • DOI

      10.1021/jo301791m

    • Related Report
      2013 Annual Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Direct Oxidation of 4-Methylpyrrole-2-carboxylates with DDQ in the presence of a Glycol.2012

    • Author(s)
      高橋香奈、岩本亮司、坂田 亮、添田貴宏、猪股勝彦、宇梶 裕
    • Journal Title

      Heterocycles

      Volume: 86 Pages: 1031-1038

    • NAID

      120005327229

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] An Asymmetric Intramolecular Stetter Reaction Catalyzed by a Chiral Triazolium Precatalyst Bearing a Pyridine Moiety2012

    • Author(s)
      T. Soeta
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 49 Pages: 10188-10193

    • DOI

      10.1016/j.tet.2012.09.095

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Molecular Dynamics of Octyl Urea Crystals Analyzed by Solid-State NMR2012

    • Author(s)
      大橋竜太郎, 若林 吾, 水野元博, 添田貴宏, 他
    • Journal Title

      Chem. Lett

      Volume: 41 Issue: 11 Pages: 1433-1435

    • DOI

      10.1246/cl.2012.1433

    • NAID

      130004426391

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Structure-Based Design, Synthesis and Characterization of Dual Hotspot Small-Molecule HIV-1 Entry Inhibitors2012

    • Author(s)
      添田貴宏、Amos B. Smith III 他
    • Journal Title

      J. Med. Chem

      Volume: 55 Issue: 9 Pages: 4382-4396

    • DOI

      10.1021/jm300265j

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] [5+1] Cycloaddition of C, N-Cyclic N'-Acyl Azomethine Imines with Isocyanides.2012

    • Author(s)
      T. Soeta, K. Tamura, Y. Ukaji
    • Journal Title

      Org. Lett

      Volume: 14 Issue: 5 Pages: 1226-1229

    • DOI

      10.1021/ol2034542

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Strecker-Type Reaction of Nitrones Using Cyanohydrin2012

    • Author(s)
      T. Sakai, T. Soeta, K. Inomata, Y. Ukaji
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 85 Issue: 2 Pages: 231-235

    • DOI

      10.1246/bcsj.20110270

    • NAID

      130004153032

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Benzoin Condensation Promoted by Chiral Triazolium Precatalyst Bearing a Pyridine Moiety2012

    • Author(s)
      T. Soeta, Y. Tabatake, K. Inomata, Y. Ukaji
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 3 Pages: 894-899

    • DOI

      10.1016/j.tet.2011.11.028

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [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2014

    • Author(s)
      奥野巧, 添田貴宏, 宇梶裕
    • Organizer
      日本化学会第94会春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Final Research Report
  • [Presentation] パラジウム-銅触媒を用いた新規アルコキシカルボニル化反応の開発2014

    • Author(s)
      古屋智樹, 添田貴宏, 遠藤恆平, 宇梶裕
    • Organizer
      日本化学会第94会春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Final Research Report
  • [Presentation] O-Phosohinative Passerini/Pudovik反応の開発 : α-ヒドロキシホスフィンアミド誘導体の高効率的one-pot合成2014

    • Author(s)
      松崎駿介, 添田貴宏, 宇梶裕
    • Organizer
      日本化学会第94会春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Final 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2014

    • Author(s)
      奥野 巧,添田貴宏,宇梶 裕
    • Organizer
      日本化学会第94回春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] パラジウム-銅触媒を用いた新規アルコキシカルボニル化反応の開発2014

    • Author(s)
      古屋智樹,添田貴宏,遠藤恆平,宇梶 裕
    • Organizer
      日本化学会第94回春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] O-Phosohinative Passerini/Pudovik型反応の開発 : α-ヒドロホスフィンアミド誘導体の高効率的one-pot合成2014

    • Author(s)
      松崎駿介,添田貴宏,宇梶 裕
    • Organizer
      日本化学会第94回春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 含窒素複素環カルベンを用いた新規な有機触媒反応の開発2013

    • Author(s)
      添田貴宏, 田畠雄太, 宇梶裕
    • Organizer
      第104回有機合成シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2013 Final Research Report
  • [Presentation] 有機ケイ素化合物を活性化剤とした新規Ugi型反応の開発2013

    • Author(s)
      田村要, 添田貴宏, 宇梶裕
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      岐阜
    • Related Report
      2013 Final Research Report
  • [Presentation] 新規なイソシアニドの付加-捕捉手法を基盤とする複素環合成反応の開発2013

    • Author(s)
      田村要, 添田貴宏, 宇梶裕
    • Organizer
      平成25年度有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Related Report
      2013 Final Research Report
  • [Presentation] 酒石酸誘導体を不斉源として活用するアゾメチンイミンの不斉1,3-双極子付加環化反応2013

    • Author(s)
      吉田麻里, 佐々直太朗, 加藤智光, 添田貴宏, 猪股勝彦, 宇梶裕
    • Organizer
      平成25年度有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Related Report
      2013 Final Research Report
  • [Presentation] Magnesium-Tartramide Complex Mediated Asymmetric Strecker-Type Reaction of Nitrones Using Cyanohydrin2013

    • Author(s)
      Takahiro Sakai, Takahiro Soeta, Kohei Endo, Shuhei Fujinami, Yutaka Ukaji
    • Organizer
      The 10 th International Symposium on Carbanion Chemistry (ISCC-10)
    • Place of Presentation
      Kyoto
    • Related Report
      2013 Final Research Report
  • [Presentation] N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with Carbodiimides under Aerobic Conditions : Efficient Synthesis of N-Acylureas2013

    • Author(s)
      Takahiro Soeta, Yuta Tabatake, Yutaka Ukaji
    • Organizer
      1^<st> International Conference & 6^<th> Symposium on Organocatalysis
    • Place of Presentation
      Otsu
    • Related Report
      2013 Final Research Report
  • [Presentation] N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with Carbodiimides under Aerobic Conditions: Efficient Synthesis of N-Acylureas2013

    • Author(s)
      Takahiro Soeta, Yuhta Tabatake, Shuhei Fujinami, Yutaka Ukaji
    • Organizer
      第1回 国際会議 (兼) 第6回 有機触媒シンポジウム
    • Place of Presentation
      滋賀県大津市 大津プリンスホテル
    • Related Report
      2013 Annual Research Report
  • [Presentation] 有機ケイ素化合物を活用した新規Ugi型反応の開発2013

    • Author(s)
      田村 要,添田貴宏,宇梶 裕
    • Organizer
      複素環化学討論会
    • Place of Presentation
      長良川国際会議場
    • Related Report
      2013 Annual Research Report
  • [Presentation] 含窒素複素環カルベンを用いた新規な有機触媒反応の開発2013

    • Author(s)
      添田貴宏・田畠雄太・宇梶 裕
    • Organizer
      第104回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Related Report
      2013 Annual Research Report
  • [Presentation] N-ヘテロサイクリックカルベン触媒を 用いたアルデヒドとカルボジイミドの 酸化的カップリング反応: N-アシルウレアの効率的合成法の開発2013

    • Author(s)
      田畠雄太・添田貴宏・宇梶 裕
    • Organizer
      日本化学会第93回春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
  • [Presentation] 酒石酸エステルを不斉源として活用する アゾメチンイミンの 不斉 1,3-双極子付加環化反応2013

    • Author(s)
      吉田麻理・佐々直太郎・加藤智光・添田貴宏・猪股勝彦・宇 梶裕
    • Organizer
      日本化学会第93回春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
  • [Presentation] アシルアジリジンより発生するアゾ メチンイリドの 1,3-双極子付加環化反応2013

    • Author(s)
      宮本祥明・和田展広・添田貴宏・猪股勝彦・宇梶 裕
    • Organizer
      日本化学会第93回春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
  • [Presentation] 酒石酸アミド-マグネシウム錯体を不斉源 とするニトロンとシアノヒドリンの 不斉 Strecker 型反応2013

    • Author(s)
      坂井飛大・添田貴宏・遠藤恆平・宇梶 裕
    • Organizer
      日本化学会第93回春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
  • [Presentation] 「シン効果」を活用した Z 選択的 ビニルトリフラート化反応の開発と応用2013

    • Author(s)
      黒澤 史也・中野 健央・添田 貴宏・遠藤 恆平・宇梶 裕
    • Organizer
      日本化学会第93回春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
  • [Presentation] イソシアニドと N-アシルイミン等価体と の触媒的[4+1]付加環化反応; 5-アミノオ キサゾール誘導体の効率的合成法の開発2013

    • Author(s)
      田村 要・添田貴宏・宇梶 裕
    • Organizer
      日本化学会第93回春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
  • [Presentation] グリコール存在下 DDQ を用いた 4-メチルピロール-2-カルボン酸エステル の酸化反応2013

    • Author(s)
      高橋香奈・岩本亮司・坂田 亮・添田貴宏・猪股勝彦・宇梶 裕
    • Organizer
      日本化学会第93回春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
  • [Presentation] C,N-環状 N'-アシルアゾメチンイミンとイソシアニドの[5+1]付加環化反応とその応用2012

    • Author(s)
      Takahiro Soeta, Kaname Tamura, Yutaka Ukaji
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] [5+1] Cycloaddition of C,N-Cyclic N'-Acyl Azomethine Imines with Isocyanides and its application2012

    • Author(s)
      Takahiro Soeta, Kaname Tamura, Yutaka Ukaji
    • Organizer
      日本プロセス化学会 2012サマーシンポジウム
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Book] Methods and Applications of Cycloaddition Reactions in Organic Syntheses."Chap.11, Development of New Methods for the Construction of Heterocycles Based on Cycloaddition Reaction of 1,3-Dipoles2014

    • Author(s)
      Yutaka Ukaji, Takahiro Soeta
    • Publisher
      Wiley
    • Related Report
      2013 Final Research Report
  • [Book] Methods and Applications of Cycloaddition Reactions in Organic Syntheses,2014

    • Author(s)
      Takahiro Soeta, Yutaka Ukaji
    • Total Pages
      28
    • Publisher
      Wiley
    • Related Report
      2013 Annual Research Report

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Published: 2013-05-31   Modified: 2019-07-29  

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