A Novel Magnetic Immobilized Para-Aminobenzoic Acid-Cu(II) Complex: A Green, Efficient and Reusable Catalyst for Aldol C
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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 Zohreh Esam1,2 · Malihe Akhavan1 · Ahmadreza Bekhradnia1,3 · Masoud Mohammadi4 · Saeed Tourani1 Received: 28 February 2020 / Accepted: 4 April 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
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 F e3O4@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 F e3O4 MNPs ( Fe3O4@PABA-Cu(II)) catalyst in Green media.
H N
O Fe3O4
O
Ar
MNPs
S
O H
or
+
H N
O HN
Ar
EtOH, 100°C
TZD Fe3O4
O
MNPs
Hydantoin
O O O O
O
NH2
OAC
NH2
Fe3O4@PABA-Cu(II)
S HN O Ar
OAC O
NH HN O
Keywords Aldol condensation · Fe3O4@PABA-Cu(II) · Magnetic nanocatalyst · 5-Arylidenthiazolidine-2,4-diones · 5-Arylidene-2-imidazolidine-2,4-dione Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10562-020-03216-w) contains supplementary material, which is available to authorized users. * Malihe Akhavan [email protected] Extended author information available on the last page of the article
1 Introduction In recent years, catalytic reactions and various metal catalysts, such as nickel, cobalt, palladium, and, top of all, copper as a cheap source of the catalytic species, have received
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considerable industrial applications and increasing attention in fundamental (basic) researches [1–6]. Despite all the advantages these catalysts have, especially good results, isolation and recovery of these tiny particles from the reaction mixture are painstaking since they cannot be efficiently filtered out of the reaction medium [7–10]. Thus, metal pollution of products is one of our major problems with this condition [2, 3, 11–13].Th
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