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A Novel Magnetic Immobilized Para-Aminobenzoic Acid-Cu(II) Complex: A Green, Efficient and Reusable Catalyst for Aldol Condensation Reactions in Green Media

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Abstract

In this the study a novel, efficient and recoverable heterogeneous nanocatalyst with regards to green chemistry purpose was approached. The structure of the newly synthesized heterogeneous magnetic nanocatalyst with enhanced and improved catalytic efficiency were determined by various instrumental techniques, including SEM, VSM, TGA, XRD, UV–VIS FT-IR and EDXA. The results, showed that the synthesized nanoparticles are superparamagnetic with a size range of 10–20 nm. Then the catalytic activity and efficient performance of Fe3O4@PABA-Cu(II) MNPs were analyzed toward the synthesis of novel 5-arylidenthiazolidine-2,4-diones and 5-arylidene-2-imidazolidine-2,4-dione derivatives via aldol condensation reactions between a variety of (hetero) aromatic aldehydes and hydantoin or thiazolidine-2,4-dione multifunctional privileged scaffolds under reflux condensations in ethanol as a benign solvent. Nontoxic nature and environment-friendly properties of the catalyst, simple workup, short time of reaction, easy separation of the catalyst from products, efficiency, and excellent yields are beneficial aspects of this method.

Graphic Abstract

It is the first report of aldol synthesis of new 5-arylidenthiazolidine-2,4-dione, and 5-arylidene-imidazolidine-2,4-dione derivatives using a reusable copper-PABA complex supported on Fe3O4 MNPs (Fe3O4@PABA-Cu(II)) catalyst in Green media.

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Authors and Affiliations

  1. Department of Medicinal Chemistry, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran

    Zohreh Esam, Malihe Akhavan, Ahmadreza Bekhradnia & Saeed Tourani

  2. Department of Medicinal Chemistry, Faculty of Pharmacy, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran

    Zohreh Esam

  3. Department of Chemistry and Biochemistry, Montana State University, 103CBB, Bozeman, MT, 59717, USA

    Ahmadreza Bekhradnia

  4. Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran

    Masoud Mohammadi

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  1. Zohreh Esam
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  2. Malihe Akhavan
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Esam, Z., Akhavan, M., Bekhradnia, A. et al. A Novel Magnetic Immobilized Para-Aminobenzoic Acid-Cu(II) Complex: A Green, Efficient and Reusable Catalyst for Aldol Condensation Reactions in Green Media. Catal Lett 150, 3112–3131 (2020). https://doi.org/10.1007/s10562-020-03216-w

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