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An Improved Synthesis of Arenedicarboximides by Phosphine-Assisted Annulation of Arene-1,2-Dicarbaldehyde with N-Substituted Maleimide

Received: 30 October 2014     Accepted: 15 November 2014     Published: 18 November 2014
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Abstract

Various arene-1,2-dicarbaldehydes react with N-substituted maleimides in the presence of trialkylphosphine in refluxing dioxane to afford the title compounds in good yields, which are better than those in a similar reaction using triethylphosphite reported by Haddadin et al. Many products were isolated by direct filtration from the reaction mixtures and washing with a suitable solvent. Application of the method to synthesis of diimides is also reported.

Published in Modern Chemistry (Volume 2, Issue 4)
DOI 10.11648/j.mc.20140204.11
Page(s) 29-35
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2014. Published by Science Publishing Group

Keywords

Maleimides, Arene-1,2-Dicarbaldehydes, Morita-Baylis-Hillman Reaction, Intramolecular Wittig Reaction

References
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Cite This Article
  • APA Style

    Mitsunori Oda, Haruki Shimosasa, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake. (2014). An Improved Synthesis of Arenedicarboximides by Phosphine-Assisted Annulation of Arene-1,2-Dicarbaldehyde with N-Substituted Maleimide. Modern Chemistry, 2(4), 29-35. https://doi.org/10.11648/j.mc.20140204.11

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    ACS Style

    Mitsunori Oda; Haruki Shimosasa; Yoshimitsu Kumai; Akira Ohta; Ryuta Miyatake. An Improved Synthesis of Arenedicarboximides by Phosphine-Assisted Annulation of Arene-1,2-Dicarbaldehyde with N-Substituted Maleimide. Mod. Chem. 2014, 2(4), 29-35. doi: 10.11648/j.mc.20140204.11

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    AMA Style

    Mitsunori Oda, Haruki Shimosasa, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake. An Improved Synthesis of Arenedicarboximides by Phosphine-Assisted Annulation of Arene-1,2-Dicarbaldehyde with N-Substituted Maleimide. Mod Chem. 2014;2(4):29-35. doi: 10.11648/j.mc.20140204.11

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  • @article{10.11648/j.mc.20140204.11,
      author = {Mitsunori Oda and Haruki Shimosasa and Yoshimitsu Kumai and Akira Ohta and Ryuta Miyatake},
      title = {An Improved Synthesis of Arenedicarboximides by Phosphine-Assisted Annulation of Arene-1,2-Dicarbaldehyde with N-Substituted Maleimide},
      journal = {Modern Chemistry},
      volume = {2},
      number = {4},
      pages = {29-35},
      doi = {10.11648/j.mc.20140204.11},
      url = {https://doi.org/10.11648/j.mc.20140204.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20140204.11},
      abstract = {Various arene-1,2-dicarbaldehydes react with N-substituted maleimides in the presence of trialkylphosphine in refluxing dioxane to afford the title compounds in good yields, which are better than those in a similar reaction using triethylphosphite reported by Haddadin et al. Many products were isolated by direct filtration from the reaction mixtures and washing with a suitable solvent. Application of the method to synthesis of diimides is also reported.},
     year = {2014}
    }
    

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    T1  - An Improved Synthesis of Arenedicarboximides by Phosphine-Assisted Annulation of Arene-1,2-Dicarbaldehyde with N-Substituted Maleimide
    AU  - Mitsunori Oda
    AU  - Haruki Shimosasa
    AU  - Yoshimitsu Kumai
    AU  - Akira Ohta
    AU  - Ryuta Miyatake
    Y1  - 2014/11/18
    PY  - 2014
    N1  - https://doi.org/10.11648/j.mc.20140204.11
    DO  - 10.11648/j.mc.20140204.11
    T2  - Modern Chemistry
    JF  - Modern Chemistry
    JO  - Modern Chemistry
    SP  - 29
    EP  - 35
    PB  - Science Publishing Group
    SN  - 2329-180X
    UR  - https://doi.org/10.11648/j.mc.20140204.11
    AB  - Various arene-1,2-dicarbaldehydes react with N-substituted maleimides in the presence of trialkylphosphine in refluxing dioxane to afford the title compounds in good yields, which are better than those in a similar reaction using triethylphosphite reported by Haddadin et al. Many products were isolated by direct filtration from the reaction mixtures and washing with a suitable solvent. Application of the method to synthesis of diimides is also reported.
    VL  - 2
    IS  - 4
    ER  - 

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Author Information
  • Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan

  • Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan

  • Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan

  • Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan

  • Centre for Environmental Conservation and Research Safety, University of Toyama, Gofuku 3190, Toyama 930-8555, Japan

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