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Novel Construction of Fused Pyridine Alkaloid Skeletons via Hetero Diels-Alder Reaction of Isotellurazoles

Research Project

Project/Area Number 23550039
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

SHIMADA Kazuaki  岩手大学, 工学部, 教授 (10142887)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2011: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywordsイソテルラゾール / ヘテロ環化付加 / 多置換ピリジン / Friedel-Crafts環化 / 縮環ピリジン類 / 縮環ピリジン系アルカロイド
Research Abstract

Hetero Diels-Alder reaction of isotellurazoles are recognized as a novel method for the regioselective synthesis of substituted pyridines, and we just attempted the expansion of the new methodology to the short-step synthesis of fused pyridine alkaloid skeletons. After an enormous efforts of our research work, we just attempted and succeeded in the short-step synthesis of fused pyridine alkaloid skeletons by using our original hetero Diels-Alder reaction of isotellurazoles and suitably designed electron-deficient acetylenic dienophiles as the important key step. Furthermore, we could find the subsequent Friedel-Crafts ring closure of the resulting pyridine ring bearing an aryl and ester groups on the suitable positions, and a convenient and short-step synthesis of a few fused pyridine alkaloid skeletons, i.e. b- and d-carbolines, 1- and 4-azafluorenones, 1-azaphenanthrenes, 1-azaanthraquinones, were finally achieved under a rather mild reaction conditions through our methodology.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (42 results)

All 2014 2013 2012 Other

All Journal Article (8 results) (of which Peer Reviewed: 6 results) Presentation (30 results) (of which Invited: 2 results) Remarks (4 results)

  • [Journal Article] Synthesis of Sterically-Crowded Olefins, gem-Dihaloalkenes, Butatrienes, and Thioketenes through the Reaction of Bornane-2-thiones or Bornane-2-selones with Conventional Carbenes or Metal Carbenoids2013

    • Author(s)
      Kazuaki Shimada, Jun Sasaki, Anna Kishi, Shigenobu Aoyagi, and Yuji Takikawa
    • Journal Title

      Natural Product Communications

      Volume: 8 (7) Pages: 851-858

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] SnCl4-Induced Unsymmetrical Cleavage of Bis(N,N-diethylcarbamoyltelluro)arylmethanes: Generation of Telluroaldehydes.2013

    • Author(s)
      Kazuaki Shimada, Takumi Higashi, Yaling Gong, Shigenobu Aoyagi, Yuji Takikawa, and Satoshi Ogawa
    • Journal Title

      Heteroatom Chemistry

      Volume: 24 (6) Issue: 6 Pages: 482-489

    • DOI

      10.1002/hc.21115

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Seleno- and Tellurocarbonic Acids and Derivatives2013

    • Author(s)
      Kazuaki Shimada
    • Journal Title

      Science of Synthesis, Knowledge Updates, Schaumann, E., Ed., Thieme, Stuttgart

      Volume: 2013/2 Pages: 289-328

    • Related Report
      2013 Final Research Report
  • [Journal Article] Synthesis of Sterically-Crowded Olefins, gem-Dihaloalkenes, Butatrienes, and Thioketenes through the Reaction of Substituted Bornane-2-thiones or Bornane-2-selones with Conventional Carbenes or Metal Carbenoids.2013

    • Author(s)
      Kazuaki Shimada, Jun Sasaki, Anna Kishi, Shigenobu Aoyagi, and Yuji Takikawa
    • Journal Title

      Natural Product Communications

      Volume: 8 (7) Pages: 851-858

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The shielding effect of fluoroaromatic rings in NMR.2013

    • Author(s)
      Toshinobu Korenaga, Fuminao Kobayashi, Kenji Nomura, Takashi Sakai, and Kazuaki Shimada
    • Journal Title

      Journal of Fluorine Chemistry

      Volume: 156 (1) Pages: 1-4

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to a,b-unsaturated carbonyl compounds was achieved at temperatures below 0 C using a Rh/MeO-F12-BIPHEP catalyst.2013

    • Author(s)
      Toshinobu Korenaga, Aramu Ko, and Kazuaki Shimada
    • Journal Title

      Journal of Organic Chemistry

      Volume: 78 (19) Issue: 19 Pages: 9975-9980

    • DOI

      10.1021/jo4014707

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Seleno- and Tellurocarbonic Acids and Derivatives2013

    • Author(s)
      Kazuaki Shimada
    • Journal Title

      Science of Synthesis, Knowledge Updates

      Volume: 2013/2 Pages: 289-328

    • Related Report
      2013 Annual Research Report
  • [Journal Article] Synthesis of Sterically-Crowded Olefins, gem-Dihaloalkenes, Butatrienes, and Thioketenes through the Reaction of Substituted Bornane-2-thiones or Bornane-2-selones with Conventional Carbenes or Metal Carbenoids2013

    • Author(s)
      Kazuaki Shimada, Jun Sasaki, Anna Kishi, Shigenobu Aoyagi and Yuji Takikawa
    • Journal Title

      Natural Products Communications

      Volume: 8 Pages: 1-8

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] イソテルラゾールのヘテロ Diels-Alder 反応をキーステップとする種々の縮環ピリジンアルカロイド骨格の短段階構築2014

    • Author(s)
      嶋田和明・種市祐介・是永敏伸
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      愛知県名古屋市, 名古屋大学東山キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of 2, 3-Dihydro-1, 2, 4-thiadiazoles and 1, 2, 4-Oxadiazoles through Oxidative Cyclization of 1, 3-Thiaza-1, 3-butadienss2013

    • Author(s)
      Isogami Megumi, Kazuaki Shimada, and Toshinobu Korenaga
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan (平成25年度化学系学協会東北大会および日本化学会東北支部 70 周年記念国際会議)
    • Place of Presentation
      仙台市, 東北大学川内キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] One Step Synthesis of α, β-Unsaturated Carbodichalcogenoate Esters from Propargyl Ethers2013

    • Author(s)
      Fumiya Ishikawa, Kazuaki Shimada, and Toshinobu Korenaga
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan (平成25年度化学系学協会東北大会および日本化学会東北支部 70 周年記念国際会議)
    • Place of Presentation
      仙台市, 東北大学川内キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] プロパジエンカルコゲノン中間体の発生と環化を経るヤエキノロン類の全合成2013

    • Author(s)
      嶋田和明・和泉大典・是永敏伸
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県草津市, 立命館大学琵琶湖草津キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] プロパジエンカルコゲノン中間体の発生と環化を経るヤエキノロン類の全合成2013

    • Author(s)
      嶋田和明・和泉大典・是永敏伸
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県、草津、立命館大学草津キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] プロパルギルエーテルからの1段階化学変換による新規なa,b-不飽和ジチオ酸エステル類の合成2013

    • Author(s)
      嶋田和明・石川郁弥・是永敏伸
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県、草津、立命館大学草津キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] Novel Generation and Trapping of Highly Reactive Chalcogenocarbonyl Intermediates2013

    • Author(s)
      Kazuaki Shimada
    • Organizer
      nvited Lecture in Bangladesh University of Engineering and Technology (BUET)
    • Place of Presentation
      Bangladesh, Dhaka, Bangladesh University of Engineering and Technology
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 置換プロパルギルエーテルを用いるα, β-不飽和ジチオ酸エステル類のワンポット合成とそれらをヘテロジエンに用いる含イオウ複素環化合物の合成への応用2012

    • Author(s)
      嶋田和明・石川郁弥・是永敏伸
    • Organizer
      第39回有機典型元素化学討論会
    • Place of Presentation
      盛岡市, アイーナ
    • Related Report
      2013 Final Research Report
  • [Presentation] プロパジエンカルコゲノン中間体を経るα-キノリノンアルカロイド骨格の簡便合成2012

    • Author(s)
      嶋田和明・和泉大典・是永敏伸
    • Organizer
      第39回有機典型元素化学討論会
    • Place of Presentation
      盛岡市, アイーナ
    • Related Report
      2013 Final Research Report
  • [Presentation] プロパジエンカルコゲノンの発生と環化を経る 2-キノリンカルコゲノン類の短段階合成2012

    • Author(s)
      嶋田和明・和泉大典・是永敏伸
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都市, 京都テルサ
    • Related Report
      2013 Final Research Report
  • [Presentation] イソテルラゾールとアセチレン系ジエノフィルのヘテロ環化付加をキーステップとする縮環ピリジン系アルカロイド骨格の短段階構築2012

    • Author(s)
      嶋田和明
    • Organizer
      平成23年度化学系学協会東北大会
    • Place of Presentation
      仙台市, 東北大学川内キャンパス
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] A Novel Synthesis of α, β-Unsaturated Chalcogenoamides by Treating Propargyl Methyl Ethers with a Base, and Elemental Chalcogen, and a Primary Amine2012

    • Author(s)
      Kazuaki Shimada, Hironori Izumi, and Fumiya Ishikawa
    • Organizer
      25th International Symposium on the Organic Chemistry of Sulfur (ISOCS)
    • Place of Presentation
      ポーランド, チェンストホーヴァ
    • Related Report
      2013 Final Research Report
  • [Presentation] イソテルラゾールと置換ベンゾイルアセチレン類のヘテロ環化付加を用いる縮環ピリジン系アルカロイド骨格の短段階構築2012

    • Author(s)
      嶋田和明・伊藤巧・小川智
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜市, 慶應義塾大学矢上キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] A Novel Synthesis of a,b-Unsaturated Chalcogenoamides by Treating Propargyl Methyl Ethers with a Base, an Elemental Chalcogen, and a Primary or Secondary Amine.2012

    • Author(s)
      Kazuaki Shimada, Hironori Izumi, and Fumiya Ishikawa
    • Organizer
      25th Internatioanal Symposium on the Organic Chemistry of Sulfur (ISOCS-25)
    • Place of Presentation
      ポーランド、チェンストホーヴァ、ヤン・ドラゴッツ大学
    • Related Report
      2012 Research-status Report
  • [Presentation] プロパジエンカルコゲノン中間体を経るα-キノリノンアルカロイド骨格の簡便合成2012

    • Author(s)
      嶋田和明・和泉大典・是永敏伸
    • Organizer
      平成24年度化学系学協会東北大会
    • Place of Presentation
      秋田県、秋田市、秋田大学
    • Related Report
      2012 Research-status Report
  • [Presentation] 活性化学種プロパジエンチオン・セロンの発生とそれらを用いるα,β-不飽和カルコゲノカルボニル化合物の合成2012

    • Author(s)
      嶋田和明・石川郁弥・是永敏伸
    • Organizer
      平成24年度化学系学協会東北大会
    • Place of Presentation
      秋田県、秋田市、秋田大学
    • Related Report
      2012 Research-status Report
  • [Presentation] プロパジエンカルコゲノンの発生と環化を経る2-キノリンカルコゲノン類の短段階合成2012

    • Author(s)
      嶋田和明・和泉大典・是永敏伸
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都府、京都、京都テルサ
    • Related Report
      2012 Research-status Report
  • [Presentation] プロパジエンカルコゲノン中間体を経るa-キノリノンアルカロイド骨格の簡便合成2012

    • Author(s)
      嶋田和明・和泉大典・是永敏伸
    • Organizer
      第39回有機典型元素化学討論会
    • Place of Presentation
      岩手県、盛岡、アイーナ
    • Related Report
      2012 Research-status Report
  • [Presentation] 置換プロパルギルエーテルを用いるa,b-不飽和ジチオ酸エステル類のワンポット合成とそれらをヘテロジエンに用いる含イオウ複素環化合物の合成への応用2012

    • Author(s)
      嶋田和明・石川郁弥・是永敏伸
    • Organizer
      第39回有機典型元素化学討論会
    • Place of Presentation
      岩手県、盛岡、アイーナ
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of 2,3-Dihydro-1,2,4-Thiadiazoles and 1,2,4-Oxadiazoles through Oxidative Cyclization of 1,3-Thiaza-1,3-butadienes.

    • Author(s)
      Kazuaki Shimada, and Toshinobu Korenaga
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan (平成25年度化学系学協会東北大会および日本化学会東北支部70周年記念国際会議)
    • Place of Presentation
      仙台市、東北大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Synthesis of Macrocyclic Amidines through the Reaction of Alkanebisthiomides with a Silver Salt.

    • Author(s)
      Shingo Takano, Kazuaki Shimada, and Toshinobu Korenaga
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan (平成25年度化学系学協会東北大会および日本化学会東北支部70周年記念国際会議)
    • Place of Presentation
      仙台市、東北大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Low-Temperature Rh-Catalyzed Asymmetric 1,4-Addition.

    • Author(s)
      Toshinobu Korenaga, Aram Ko, and Kazuaki Shimada
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan (平成25年度化学系学協会東北大会および日本化学会東北支部70周年記念国際会議)
    • Place of Presentation
      仙台市、東北大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Pd-Catalyzed Intramolecular Direct Arylation: Acceleration of the Reaction by Electron-Poor BFPy Phosphine Ligand.

    • Author(s)
      Toshinobu Korenaga, Noriki Suzuki, and Kazuaki Shimada
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan (平成25年度化学系学協会東北大会および日本化学会東北支部70周年記念国際会議)
    • Place of Presentation
      仙台市、東北大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] One-Pot Synthesis of a,b-Unsaturated Carbodichalcogenoate Esters from Propargyl Ethers.

    • Author(s)
      Fumiya Ishikawa, Kazuaki Shimada, and Toshinobu Korenaga
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan (平成25年度化学系学協会東北大会および日本化学会東北支部70周年記念国際会議)
    • Place of Presentation
      仙台市、東北大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] α,β-不飽和ジチオ酸エステル類の簡便合成とその酸化的環化によるイソチアゾリン類への変換

    • Author(s)
      嶋田和明・石川郁弥・是永敏伸
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋市、名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 1,3-チアザ-1,3-ブタジエンの酸化的環化を経る1,3-チアゾール類の合成

    • Author(s)
      嶋田和明・磯上愛・是永敏伸
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋市、名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] イソテルラゾールのヘテロDiels-Alder反応をキーステップとする種々の縮環ピリジンアルカロイド骨格の短段階構築

    • Author(s)
      嶋田和明・種市祐介・是永敏伸
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋市、名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 電子不足なホスフィン配位子を有するパラジウム触媒による直接的分子内アリール化反応

    • Author(s)
      是永敏伸・鈴木悟基・嶋田和明
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋市、名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] イソテルラゾールとアセチレン系ジエノフィルのヘテロ環化付加をキーステップとする縮環ピリジン系アルカロイド骨格の短段階構築

    • Author(s)
      嶋田和明
    • Organizer
      平成23年度化学系学協会東北大会(招待講演)
    • Place of Presentation
      仙台市、東北大学川内キャンパス
    • Related Report
      2011 Research-status Report
  • [Presentation] イソテルラゾールと置換ベンゾイルアセチレン類のへテロ環化付加を用いる縮環ピリジン系アルカロイド骨格の短段階構築

    • Author(s)
      嶋田和明・伊藤巧・小川智
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜市、慶応義塾大学矢上キャンパス
    • Related Report
      2011 Research-status Report
  • [Remarks] 岩手大学工学部応用化学・生命工学科有機合成化学研究室HP

    • URL

      http://www.chem.iwate-u.ac.jp/web/labo/shimada/HP/index.html

    • Related Report
      2013 Final Research Report
  • [Remarks] 岩手大学工学部応用化学・生命工学科嶋田和明用 HP

    • URL

      http://www.chem.iwate-u.ac.jp/web/labo/shimada/Contents.html

    • Related Report
      2013 Final Research Report
  • [Remarks] 国立大学法人岩手大学 研究者総覧 嶋田和明

    • URL

      http://univdb.iwate-u.ac.jp/profile.php

    • Related Report
      2013 Annual Research Report
  • [Remarks] 岩手大学工学部応用化学・生命工学科 有機合成化学研究室HP

    • URL

      http://www.chem.iwate-u.ac.jp/web/labo/shimada/HP/index.html

    • Related Report
      2013 Annual Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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