An Improved Synthesis of Arenedicarboximides by Phosphine-Assisted Annulation of Arene-1,2-Dicarbaldehyde with N-Substituted Maleimide
Modern Chemistry
Volume 2, Issue 4, August 2014, Pages: 29-35
Received: Oct. 30, 2014; Accepted: Nov. 15, 2014; Published: Nov. 18, 2014
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Authors
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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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.
Keywords
Maleimides, Arene-1,2-Dicarbaldehydes, Morita-Baylis-Hillman Reaction, Intramolecular Wittig Reaction
To cite this article
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, Modern Chemistry. Vol. 2, No. 4, 2014, pp. 29-35. doi: 10.11648/j.mc.20140204.11
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