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Development of novel pi-electron deficient nitrogen-containing heterocycles for dehydrocondensations

Research Project

Project/Area Number 26293003
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKanazawa University

Principal Investigator

KUNISHIMA MUNETAKA  金沢大学, 薬学系, 教授 (10214975)

Co-Investigator(Kenkyū-buntansha) 山田 耕平  金沢大学, 薬学系, 助教 (40583232)
北村 正典  金沢大学, 薬学系, 准教授 (80453835)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥11,310,000 (Direct Cost: ¥8,700,000、Indirect Cost: ¥2,610,000)
Fiscal Year 2016: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2015: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2014: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Keywords脱水縮合剤 / トリアジン / 電子欠乏性含窒素芳香環 / アルキル化剤 / アミド / 脱水縮合 / エステル / 含窒素複素環 / 含窒素芳香環
Outline of Final Research Achievements

We have developed novel dehydrocondensing reagents related to DMT-MM, which enables us to conduct reactions between carboxylic acids and amines in aqueous or alcoholic solvents to give amides. In this research project, we succeeded in synthesizing highly activated and/or functionalized dehydrocondensing reagents by the detailed study on the substituent effect and the skeletal transformation of pi-electron-deficient triazines. Moreover, based on the obtained results, novel alkylating reagents and methods for chemical transformation were also developed.

Report

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

    (51 results)

All 2017 2016 2015 2014

All Journal Article (13 results) (of which Peer Reviewed: 13 results,  Open Access: 1 results,  Acknowledgement Compliant: 6 results) Presentation (31 results) (of which Int'l Joint Research: 7 results,  Invited: 1 results) Patent(Industrial Property Rights) (7 results)

  • [Journal Article] N,N’-Dimethylated Benzyloxytriazinedione: A Stable Solid Reagent for Acid-Catalyzed O-Benzylation2017

    • Author(s)
      Hikaru Fujita, Satoshi Kakuyama, Munetaka Kunishima
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2017 Issue: 4 Pages: 833-839

    • DOI

      10.1002/ejoc.201601387

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Study of <i>O</i>-Allylation Using Triazine-Based Reagents2017

    • Author(s)
      Kohei Yamada, Naoko Hayakawa, Hikaru Fujita, Masanori Kitamura, Munetaka Kunishima
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 65 Issue: 1 Pages: 112-115

    • DOI

      10.1248/cpb.c16-00744

    • NAID

      130005187751

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Potent triazine-based dehydrocondensing reagents substituted by an amido group2016

    • Author(s)
      Munetaka Kunishima, Daiki Kato, Nobu Kimura, Masanori Kitamura, Kohei Yamada, Kazuhito Hioki
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 12 Pages: 1897-1903

    • DOI

      10.3762/bjoc.12.179

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Development of Acid-Catalyzed Fluorous Benzylating Reagents Based on a Triazinedione Core2016

    • Author(s)
      Munetaka Kunishima, Ryohei Asao, Kohei Yamada, Masanori Kitamura, Hikaru Fujita
    • Journal Title

      J. Fluorine Chem

      Volume: 190 Pages: 68-74

    • DOI

      10.1016/j.jfluchem.2016.09.003

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hydroxy and Amino Group-Tolerant Synthesis of Six-Membered Cyclic Quaternary Ammonium Salts Using a Triazine-Based Reagent2016

    • Author(s)
      Masanori Kitamura, Seina Yamamura, Kohei Yamada, Munetaka Kunishima
    • Journal Title

      Asian J. Org. Chem.

      Volume: 5 Issue: 12 Pages: 1508-1517

    • DOI

      10.1002/ajoc.201600429

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mild Amide-Cleavage Reaction Mediated by Electrophilic Benzylation2016

    • Author(s)
      Kohei Yamada, Yukiko Karuo, Yuichi Tsukada, Munetaka Kunishima
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 39 Pages: 14042-14047

    • DOI

      10.1002/chem.201603120

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of a Triazine-based tert-Butylating Reagent, TriAT-tBu2016

    • Author(s)
      Kohei Yamada, Naoko Hayakawa, Hikaru Fujita, Masanori Kitamura, Munetaka Kunishima
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2016 Issue: 23 Pages: 4093-4098

    • DOI

      10.1002/ejoc.201600663

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Study of the Reactivities of Acid-Catalyzed O-Benzylating Reagents Based on Structural Isomers of 1,3,5-Triazine2015

    • Author(s)
      Hikaru Fujita, Naoko Hayakawa, and Munetaka Kunishima
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 21 Pages: 11200-11205

    • DOI

      10.1021/acs.joc.5b02059

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] O-Benzylation of Carboxylic Acids Using 2,4,6-Tris(benzyloxy)-1,3,5-triazine (TriBOT) under Acidic or Thermal Conditions2015

    • Author(s)
      Kohei Yamada, Saki Yoshida, Hikaru Fujita, Masanori Kitamura, and Munetaka Kunishima
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 36 Issue: 36 Pages: 7997-8002

    • DOI

      10.1002/ejoc.201501172

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Specific Labeling of Streptavidin for Better Understanding of Ligand Modification in Modular Method for Affinity Labeling (MoAL)2014

    • Author(s)
      Munetaka Kunishima, Daiki Kato, Shuichi Nakanishi, Masanori Kitamura, Kohei Yamada, Keiji Terao, Tomoya Asano
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 62 Issue: 11 Pages: 1146-1150

    • DOI

      10.1248/cpb.c14-00468

    • NAID

      130004712907

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Pyrrolidinium Salts Using a Triazine-based Reagent under Mild Conditions2014

    • Author(s)
      Masanori Kitamura, Seina Yamamura, Hiroko Kobayashi, Mariko Yamamoto, Kayo Tada, Kazuhito Hioki, Kohei Yamada, Munetaka Kunishima
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 10 Pages: 1593-1595

    • DOI

      10.1246/cl.140503

    • NAID

      130004427196

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of a New Benzylating Reagent Spontaneously Releasing Benzyl Cation Equivalents at Room Temperature2014

    • Author(s)
      Kohei Yamada, Yuichi Tsukada, Yukiko Karuo, Masanori Kitamura, Munetaka Kunishima
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 38 Pages: 12274-12278

    • DOI

      10.1002/chem.201403158

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Role of Linkers in Tertiary Amines That Mediate or Catalyze 1,3,5-Triazine-Based Amide-Forming Reactions2014

    • Author(s)
      M. Kitamura, F. Kawasaki, K. Ogawa, S. Nakanishi, H. Tanaka, K. Yamada, M. Kunishima
    • Journal Title

      J. Org. Chem

      Volume: 79 Issue: 8 Pages: 3709-3714

    • DOI

      10.1021/jo500376m

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Presentation] トリアジニルピリジニウム塩を用いたエステル化反応の開発2017

    • Author(s)
      劉杰、山田耕平、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター、仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] トリアジンジオンを基盤とする新規アシル化剤の開発2017

    • Author(s)
      古田美佳、軽尾友紀子、 李政洙、山田耕平、北村正典、国嶋 崇隆
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター、仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] 新規トリアジン型酸化剤の開発と反応2017

    • Author(s)
      五十嵐佑貴、別役樹、山田耕平、国嶋崇隆
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター、仙台
    • Related Report
      2016 Annual Research Report
  • [Presentation] アミド基を置換基に有するトリアジニルアンモニウム型脱水縮合剤の開発2016

    • Author(s)
      古田美佳, 山田耕平, 藤田光, 国嶋崇隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜、横浜
    • Year and Date
      2016-03-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] ポリアクリルアミドを担体とする親水性固定化脱水縮合剤の開発2016

    • Author(s)
      夏俊卿, 山田耕平, 国嶋崇隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜、横浜
    • Year and Date
      2016-03-28
    • Related Report
      2015 Annual Research Report
  • [Presentation] サイトⅠ特異的な薬物タンパク結合を検出する蛍光標識化アルブミンの開発2016

    • Author(s)
      瀧澤祐美佳, 山田耕平, 国嶋崇隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜、横浜
    • Year and Date
      2016-03-28
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of HSA Sensor for Detection of Site II Drug Binding.2016

    • Author(s)
      Kunishima M.
    • Organizer
      Asian Chemical Biology Initiative (ACBI) 2016 Jakarta Meeting
    • Place of Presentation
      Jakarta, Indonesia
    • Year and Date
      2016-01-30
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of triazine-type dehydrocondensing reagents having an amido group2016

    • Author(s)
      Daiki Kato, Nobu Kimura, Kohei Yamada, Masanori Kitamura, Munetaka Kunishima
    • Organizer
      XXVII European Colloquium on Heterocyclic Chemistry (ECHC 2016)
    • Place of Presentation
      Beurs van berlage, Amsterdam, Netherlands
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新規トリアジノン型脱水縮合剤の開発2016

    • Author(s)
      古田美佳、高橋 健輔、山田耕平、藤田光、国嶋崇隆
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      歌劇座、金沢
    • Related Report
      2016 Annual Research Report
  • [Presentation] カルボン酸・アミノ酸・アリールボロン酸からなる三置換オキサゾールの短工程合成法の開発2016

    • Author(s)
      上村直人、山田耕平、藤田光、国嶋崇隆
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      歌劇座、金沢
    • Related Report
      2016 Annual Research Report
  • [Presentation] 互変異性化を駆動力とした新規トリアジン型酸化剤の開発2016

    • Author(s)
      五十嵐佑貴、山田耕平、平田紘基、国嶋崇隆
    • Organizer
      日本薬学会北陸支部第128回例会
    • Place of Presentation
      北陸大学、金沢
    • Related Report
      2016 Annual Research Report
  • [Presentation] 塩化トリアジンを用いた六員環状第四級アンモニウム塩合成法の開発2016

    • Author(s)
      北村正典、山村聖奈、山田耕平、国嶋崇隆
    • Organizer
      第34回メディシナルケミストリーシンポジウム
    • Place of Presentation
      つくば国際会議場、つくば
    • Related Report
      2016 Annual Research Report
  • [Presentation] Study of the reactivity of benzyloxytriazine derivatives (BOTs) for acid catalyzed O-benzylation2015

    • Author(s)
      Fujita H, Kunishima M.
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Quick and mild methods for cleavage of amide-bonds by using a triazine-based benzylating reagent2015

    • Author(s)
      Karuo Y, Yamada K, Kunishima M.
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Effect of carbon substituents on the reactivity of triazine-based dehydrocondensing reagents2015

    • Author(s)
      Komine S, Kitamura M, Kunishima M.
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新規酸触媒トリアジノン型ベンジル化剤の開発2015

    • Author(s)
      角山哲史, 藤田光, 北村正典, 山田耕平, 国嶋崇隆
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      早稲田大学、東京
    • Year and Date
      2015-11-20
    • Related Report
      2015 Annual Research Report
  • [Presentation] 薬物タンパク結合を検出する蛍光標識化アルブミンの開発2015

    • Author(s)
      巻口真穂, 木野徹平, 山田耕平, 浅野智哉, 国嶋崇隆
    • Organizer
      日本薬学会北陸支部第127回例会
    • Place of Presentation
      富山大学、富山
    • Year and Date
      2015-11-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of acid-catalyzed alkylating reagents based on triazine chemistry2015

    • Author(s)
      Hayakawa N, Yamada K, Fujita H, Kitamura M, Yoshimura K, Kunishima M.
    • Organizer
      The 3rd International Symposium on Process Chemistry
    • Place of Presentation
      Kyoto International Conference Center, Kyoto, Japan
    • Year and Date
      2015-07-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of a method for the synthesis of trisubstituted oxazoles by Suzuki-Miyaura Coupling2015

    • Author(s)
      Yamada K, Kamimura N, Fujita H, Kunishima M.
    • Organizer
      the 18th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Barcelona, Spain
    • Year and Date
      2015-06-29
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] カルボン酸・アミノ酸・アリールボロン酸からなる三置換オキサゾール合成法の開発2015

    • Author(s)
      上村直人、山田耕平、藤田光、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、神戸学院大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 電子的効果の軽微な置換基を有するトリアジン型縮合剤の反応性に関する研究学会等名2015

    • Author(s)
      小峰彩、北村正典、岡田有加里、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、神戸学院大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 電子欠乏性トリアジニルホスフィン配位子の開発2015

    • Author(s)
      安倍一実、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、クリエイティブセンター神戸
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] トリアジン骨格を基盤とする酸触媒tert-ブチル化剤の開発2015

    • Author(s)
      早川奈緒子、山田耕平、藤田光、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、神戸学院大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] アミノトリアジンを脱離基とするベンジル化剤の開発:置換基効果に基づく分解反応の制御2015

    • Author(s)
      軽尾友紀子、小峰彩、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、神戸学院大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] π電子欠乏性新規トリアジン型脱水縮合剤の開発2015

    • Author(s)
      木村円、矢内秀、山田耕平、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸、神戸学院大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] トリアジニルアミンを脱離基とした分子内閉環反応によるピロリジニウム塩の合成2014

    • Author(s)
      山村聖奈,北村正典,小林比呂子,山本真理子,多田佳世,日置和人,山田耕平,国嶋崇隆
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台、東北大学 川内萩ホール
    • Year and Date
      2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] Development of a new benzylating reagent which releases benzyl cation-like species at room temperature2014

    • Author(s)
      Kohei Yamada, Yukiko Karuo, Yuichi Tsukada, Masanori Kitamura, Munetaka Kunishima
    • Organizer
      14th Tetrahedron Symposium Asia Edition
    • Place of Presentation
      Singapore、Singapore EXPO Convention and Exhibition Centre
    • Year and Date
      2014-10-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] 電子欠乏性アミノトリアジンを脱離基としたベンジル化剤の開発2014

    • Author(s)
      軽尾友紀子, 塚田裕以智, 山田耕平, 北村正典, 国嶋崇隆
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      北海道、札幌市民ホール
    • Year and Date
      2014-09-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] 酸触媒ベンジル化剤TriBOTを用いた低環境負荷型エステル化反応の開発2014

    • Author(s)
      山田耕平、吉田紗季、吉村和真、藤田光、北村正典、河合伸高、国嶋崇隆
    • Organizer
      日本プロセス化学会 2014 サマーシンポジウム
    • Place of Presentation
      東京、タワーホール船堀
    • Year and Date
      2014-08-01
    • Related Report
      2014 Annual Research Report
  • [Presentation] ベンジルカチオン種の求電子付加に基づくアミド結合開裂反応の開発2014

    • Author(s)
      軽尾友紀子,山田耕平,北村正典,国嶋崇隆
    • Organizer
      創薬懇話会 2014 in 岐阜
    • Place of Presentation
      岐阜、岐阜長良川温泉 ホテルパーク
    • Year and Date
      2014-07-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] 未知の薬物標的タンパク質の探索を志向した親和標識化法2014

    • Author(s)
      加藤大輝, 北村正典, 山田耕平, 浅野智哉, 国嶋崇隆
    • Organizer
      創薬懇話会 2014 in 岐阜
    • Place of Presentation
      岐阜、岐阜長良川温泉 ホテルパーク
    • Year and Date
      2014-07-09
    • Related Report
      2014 Annual Research Report
  • [Patent(Industrial Property Rights)] 酸化剤2016

    • Inventor(s)
      国嶋崇隆
    • Industrial Property Rights Holder
      国立大学法人金沢大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-210433
    • Filing Date
      2016-10-27
    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] トリアジノン化合物2016

    • Inventor(s)
      国嶋崇隆
    • Industrial Property Rights Holder
      国立大学法人金沢大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-034845
    • Filing Date
      2016-02-25
    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] トリアジン含有ポリマー、その製造方法、及びその脱水縮合剤としての用途2016

    • Inventor(s)
      国嶋崇隆
    • Industrial Property Rights Holder
      国立大学法人金沢大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-034723
    • Filing Date
      2016-02-25
    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] トリアジンジオン化合物2015

    • Inventor(s)
      国嶋崇隆
    • Industrial Property Rights Holder
      国立大学法人金沢大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-208908
    • Filing Date
      2015-10-23
    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] 脱水縮合剤2015

    • Inventor(s)
      国嶋崇隆
    • Industrial Property Rights Holder
      金沢大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-016112
    • Filing Date
      2015-01-29
    • Related Report
      2014 Annual Research Report
  • [Patent(Industrial Property Rights)] 脱水縮合剤2015

    • Inventor(s)
      国嶋崇隆
    • Industrial Property Rights Holder
      金沢大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-016113
    • Filing Date
      2015-01-29
    • Related Report
      2014 Annual Research Report
  • [Patent(Industrial Property Rights)] トリアジン化合物2015

    • Inventor(s)
      国嶋崇隆
    • Industrial Property Rights Holder
      金沢大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-037118
    • Filing Date
      2015-02-26
    • Related Report
      2014 Annual Research Report

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

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