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Synthesis of Nitroaniline Derivatives by a Built-in Method of Unstable Nitromalonaldehyde

Research Project

Project/Area Number 26410123
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionKochi University of Technology

Principal Investigator

NISHIWAKI Nagatoshi  高知工科大学, 環境理工学群, 教授 (30237763)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2015: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2014: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords環変換反応 / ニトロピリジン / ニトロアニリン / ビシクロ中間体 / ジニトロピリドン / 酢酸アンモニウム / 三成分系反応 / アルケニルピリジン / アルキニルピリジン / 多成分系反応
Outline of Final Research Achievements

Three component ring transformation of dinitropyridone, ketone, and ammonium acetate proceeded to afford nitropyridines and nitroanilines. These products are not easily available by alternative methods. To the contrary, the present method requires only simple experimental manipulations. In addition, modification of the product can be easily perfomed by only changing the ketone. Hence, it is applicable to various purposes.
The synthesized products have both electron-donating and -withdrawing groups, which brings about the biased electron density. Such frameworks are often used for biologically compounds and optical materials. Hence, the present method facilitates the development of new functional materials.

Report

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

    (10 results)

All 2017 2016 2015 2014 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 3 results) Presentation (4 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results) Remarks (1 results)

  • [Journal Article] Three-Component Ring Transformation Using Ammonium Acetate as a Nitrogen Source2016

    • Author(s)
      Nagatoshi Nishiwaki
    • Journal Title

      Targets in Heterocyclic Systems - Chemistry and Properties (THS)

      Volume: 19 Pages: 128-156

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Nitroarenes Using Three-Component Ring Transformation2016

    • Author(s)
      浅原時泰、Le Thi Song、西脇永敏
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 74 Issue: 2 Pages: 130-140

    • DOI

      10.5059/yukigoseikyokaishi.74.130

    • NAID

      130005138526

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Metal-Free Synthesis of 2-Alkenyl/Alkynyl-5-nitropyridines Using Three-Component Ring Transformation2015

    • Author(s)
      Song Thi Le, Haruyasu Asahara, Nagatoshi Nishiwaki
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 6 Pages: 776-778

    • DOI

      10.1246/cl.150045

    • NAID

      130005074567

    • Related Report
      2015 Research-status Report 2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An Alternative Synthetic Approach to 3-Alkylated/Arylated 5-Nitropyridines2015

    • Author(s)
      Song Thi Le, Haruyasu Asahara, and Nagatoshi Nishiwaki
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 17 Pages: 8856-8858

    • DOI

      10.1021/acs.joc.5b01391

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Tailor-made Synthesis of N,N,2,6-Tetrasubstituted 4-Nitroanilines by Three-Component Ring Transformation of Dinitropyridone2015

    • Author(s)
      Song Thi Le, Haruyasu Asahara, and Nagatoshi Nishiwaki
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2015 Issue: 6 Pages: 1203-1206

    • DOI

      10.1002/ejoc.201403652

    • NAID

      120005983211

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Synthesis of Versatile Aza-Heterocyclic Compounds by Three Component Ring Transformation2017

    • Author(s)
      Nagatoshi Nishiwaki
    • Organizer
      14th International Conference and Exhibition on Pharmaceutical Formulations
    • Place of Presentation
      Brussels, Belgium
    • Year and Date
      2017-08-28
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Three-Component Ring Transformation: A Powerful Method for Synthesizing Aza-Heterocyclic Compounds2015

    • Author(s)
      Nagatoshi Nishiwaki
    • Organizer
      International Congress on Heterocyclic Chemistry (KOST-2015)
    • Place of Presentation
      Moscow, Russia
    • Year and Date
      2015-10-18
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of N,N,2,6-Tetrasubstituted 4-Nitroalinines by Three Component Ring Transformation of Dinitropyridone2015

    • Author(s)
      Song Thi Le・Haruyasu Asahara・Nagatoshi Nishiwaki
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学、船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis of Nitropyridines by Three Component Ring Transformation of Dinitropyridone2014

    • Author(s)
      Song Thi Le, Haruyasu Asahara and Nagatoshi Nishiwaki
    • Organizer
      7th Eurasian Meeting on Heterocyclic Chemistry (EAMHC 2012)
    • Place of Presentation
      Tbilisi, Georgia
    • Year and Date
      2014-09-20 – 2014-09-24
    • Related Report
      2014 Research-status Report
  • [Remarks] Recent Publication

    • URL

      https://sites.google.com/site/kutnishiwakilab2/publication

    • Related Report
      2014 Research-status Report

URL: 

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

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