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

Mitsunori Oda; Haruki Shimosasa; Yoshimitsu Kumai; Akira Ohta; Ryuta Miyatake

doi:doi:10.11648/j.mc.20140204.11

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

Mitsunori Oda, Haruki Shimosasa, Yoshimitsu Kumai, Akira Ohta, Ryuta Miyatake

Published in Modern Chemistry (Volume 2, Issue 4)

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), 2024. Published by Science Publishing Group

Keywords

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

References

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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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TY  - JOUR
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

Mitsunori Oda

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

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

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

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

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

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Plain Text BibTeX RIS

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

Copy | Download

@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}
}

Copy | Download

TY  - JOUR
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  -

Copy | Download