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Heterocycle synthesis utilizing ortho-fuctionalized benzyl azides

Research Project

Project/Area Number 26410051
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionTottori University

Principal Investigator

KOBAYASHI Kazuhiro  鳥取大学, 工学(系)研究科(研究院), 准教授 (90161976)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Keywordsベンジルアジド / ヘテロ環 / 臭素ーリチウム交換 / aza-Wittig反応 / Staudinger反応 / キナゾリン / イソインドリノン / ベンゾトリアジン / イソインドール / 脱窒素 / ベンジルアニオン / ベンジリデンイミニド / ベンゾ[b]チオフェン / ベンズオキサジン / 臭素/リチウム交換 / ジヒドロイソインドール
Outline of Final Research Achievements

Ten simple and efficient methods for the general preparation of heterocyclic derivatives (cyclic compounds containing more than one hetero atom, such as nitrogen, sulfur or oxygen, in the ring(s)), which are hard or impossible to construct by previous conventional methods, utilizing ortho-functionalized benzyl azides (benzene derivatives having a azidomethyl: -CH2N3 group and a functional (labile) group adjacent to each other of the benzene ring) have been developed. The benzyl azides can be prepared from readily available starting materials utilizing simplly operational sequences. The products prepared are of highly potential use for creation of new medicines or agricultural medicines.

Report

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

    (15 results)

All 2016 2015 2014

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Acknowledgement Compliant: 9 results) Presentation (6 results)

  • [Journal Article] Synthesis of N,N-Disubstituted 1-Aryl-1,3-dihydro-2H-isoindole-2-carbothioamides2016

    • Author(s)
      Kazuhiro Kobayashi, Yuuho Shigemura, Miyuki Tanmatsu
    • Journal Title

      Heterocycles

      Volume: 92 Issue: 5 Pages: 844-856

    • DOI

      10.3987/com-16-13421

    • NAID

      40020825856

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A convenient synthesis of 2-alkyl-3-aryl-2,3-dihydro-1H-isoindol-1-ones by the reaction of N-alkyl-N-[(2-bromophenyl)methyl]benzamides with butyllithium2016

    • Author(s)
      Kazuhiro Kobayashi, Yuuki Chikazawa
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 33 Pages: 5100-5105

    • DOI

      10.1016/j.tet.2016.06.082

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] One-Pot Synthesis of 3-Substituted 3,4-Dihydro-1,2,3-benzotoriazine Derivatives Based on the Reaction of o-Bromobenzyl Azides with Butyllithium2016

    • Author(s)
      Kazuhiro Kobayashi, Yuuki Chikazawa
    • Journal Title

      Helvetica Chimica Acta

      Volume: 99 Issue: 1 Pages: 33-36

    • DOI

      10.1002/hlca.201500234

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 3,4-Dihydro-2H-1,3-benzoxazine-2-thiones via Cyclization of 2-(1-Isothiocyanatoalkyl)phenols2016

    • Author(s)
      Kazuhiro Kobayashi, Hiroki Inouchi, Naoki Matsumoto
    • Journal Title

      Heterocycles

      Volume: 93 Issue: 1 Pages: 63-63

    • DOI

      10.3987/com-15-s(t)2

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] One-Pot Synthesis of 3-Alkoxy-2,3-dihydro-1H-isoindol-1- ones by the Reactions of 2-(Azidomethyl)benzoates with NaH2015

    • Author(s)
      Kazuhiro Kobayashi, Yuuki Chikazawa, Kosuke Ezaki
    • Journal Title

      Helvetica Chimica Acta

      Volume: 98 Issue: 5 Pages: 604-610

    • DOI

      10.1002/hlca.201500051

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] One-Pot Synthesis of 3-Acetyl-2-aryl-3,4-dihydroquinazolines from N-[2-(Azidomethyl)phenyl]benzamides Utilizing Intramolecular Aza-Wittig Reaction2015

    • Author(s)
      Kazuhiro Kobayashi, Naoki Matsumoto, Mika Nagashima, Hiroki Inouchi
    • Journal Title

      Helvetica Chimica Acta

      Volume: 98 Issue: 2 Pages: 184-190

    • DOI

      10.1002/hlca.201400316

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Novel Synthesis of Quinazolines by Cyclization of 1-(2-Isocyanophenyl)alkylideneamines Generated by the Treatment of 2-(1-Azidoalkyl)phenyl Isocyanides with NaH2014

    • Author(s)
      Kosuke Ezaki, Kazuhiro Kobayashi
    • Journal Title

      Helvetica Chimica Acta

      Volume: 97 Issue: 6 Pages: 822-829

    • DOI

      10.1002/hlca.201300431

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 1-Acyl-3,4-dihydroquinazoline-2(1H)-thiones by Cyclization of N-[2-(Isothiocyanatomethyl)phenyl] Amides Generated in situ from N-[2-(Azidomethyl)phenyl] Amides2014

    • Author(s)
      Kazuhiro Kobayashi, Naoki Matsumoto
    • Journal Title

      Helvetica Chimica Acta

      Volume: 97 Issue: 7 Pages: 923-930

    • DOI

      10.1002/hlca.201400078

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2-Substituted 3-Alkylidene-2,3-dihydro-1H-isoindol-1-imines through Cyclization of [1-(2-Cyanophenyl)-alkylidene]aminide Intermediates Generated from the Reaction of 2-(1-Azidoalkyl)benzonitriles with NaH2014

    • Author(s)
      Kazuhiro Kobayashi, Kosuke Ezaki, Ippei Nozawa
    • Journal Title

      Helvetica Chimica Acta

      Volume: 97 Issue: 12 Pages: 1624-1629

    • DOI

      10.1002/hlca.201400261

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] o-アルキルスルホニルベンジルアジドのLDAによる脱プロトン化で開始される合成反応2016

    • Author(s)
      近澤 優輝・小林 和裕
    • Organizer
      2016年日本化学会中国四国支部大会
    • Place of Presentation
      高松市幸町1-1 香川大学幸町キャンパス
    • Year and Date
      2016-11-05
    • Related Report
      2016 Annual Research Report
  • [Presentation] ベンゾ[c]チオフェン-1(3H)-イミンおよびイソインドール-2-カルボチオアミド誘導体の合成2015

    • Author(s)
      重村 雄歩・江﨑 光佑・小林 和裕
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      東京都新宿区西早稲田1-6-1 早稲田大学 国際会議場
    • Year and Date
      2015-11-19
    • Related Report
      2015 Research-status Report
  • [Presentation] o-ブロモベンジルアジドを用いる1,2,3-ベンゾトリアジン及びイソインドリノン誘導体の合成2015

    • Author(s)
      近澤 優輝・小林 和裕
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      東京都新宿区西早稲田1-6-1 早稲田大学 国際会議場
    • Year and Date
      2015-11-19
    • Related Report
      2015 Research-status Report
  • [Presentation] o-リチオベンジルアジドの環化による1-アシル-1,4-ジヒドロ-1,2,3-ベンゾトリアジンの合成2015

    • Author(s)
      近澤優輝・小林和裕
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋市習志野台 日本大学 理工学部船橋キャンパス/薬学部
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 2-(アジドメチル)ベンゾエート誘導体の脱窒素-環化による3-アルコキシイソインドリノンの合成2015

    • Author(s)
      井ノ内宏樹・近澤優輝・江崎光佑・小林和裕
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋市習志野台 日本大学 理工学部船橋キャンパス/薬学部
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] o-(1-イソチオシアナートアルキル)フェノール誘導体の環化による3,4-ジヒドロ-2H-1,3-ベンズオキサジン-2-チオン誘導体の合成2014

    • Author(s)
      井ノ内宏樹・松本直記・小林和裕
    • Organizer
      2014年日本化学会中国四国支部大会
    • Place of Presentation
      山口市吉田1677-1 山口大学吉田キャンパス
    • Year and Date
      2014-11-08 – 2014-11-09
    • Related Report
      2014 Research-status Report

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

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