Synthesis of Fe 3 O 4 -supported Schiff base Cu (II) complex: a novel efficient and recyclable magnetic nanocatalyst for
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Synthesis of Fe3O4‑supported Schiff base Cu (II) complex: a novel efficient and recyclable magnetic nanocatalyst for one‑pot three‑component synthesis of quinolin‑5‑one, chromene‑3‑carbonitrile and phthalazine‑5,10‑dione derivatives Hakimeh Ebrahimiasl1 · Davood Azarifar1 · Mahsa Mohammadi1,2,3 · Hassan Keypour1 · Masoumeh Mahmood abadi1 Received: 4 August 2020 / Accepted: 3 October 2020 © Springer Nature B.V. 2020
Abstract In this research, synthesis and characterization of a novel Schiff base Cu (II) complex immobilized on F e3O4@SiO2 nanoparticles are reported. Then, the catalytic activity of these nanoparticles as magnetic recyclable nanocatalyst was explored for the one-pot three-component synthesis of quinolin-5-one, chromene-3-carbonitrile and phthalazine-5,10-dione derivatives. The reactions proceeded smoothly to provide the respective products in excellent yields under green conditions. Facile preparation of the catalyst, high yields of the products, low reaction times, and use of water as green solvent are the main advantages of the present protocol. Moreover, the catalyst can be easily separated from the reaction mixture in a magnetic field, recycled and reused for six consecutive fresh runs without considerable loss of catalytic activity.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04293-7) contains supplementary material, which is available to authorized users. * Hakimeh Ebrahimiasl [email protected] 1
Department of Chemistry, Bu-Ali Sina University, 65178 Hamedan, Iran
2
Pharmaceutical Sciences Research Center, School of Pharmacy, Health Institute, Kermanshah University of Medical Sciences, Kermanshah, Iran
3
Department of Medicinal Chemistry, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran
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Graphic abstract
Keywords Fe3O4-supported cu (II) Schiff–base complex · Magnetic nanoparticles · Multicomponent reaction · Quinolin-5-one · Chromene-3-carbonitrile · Phthalazine5,10-dione
Introduction In chemistry, quite often, ligands include with a ring size of nine or more atoms (containing hetero atoms) and contain at least three donor sites [1]. So far, a variety of synthetic and natural compounds such as crown ethers, Schiff bases and porphyrins have been investigated [2]. Several compounds and their derivatives exhibit high affinity for metal ions and host various neutral molecules and organic cation guests and are also useful in phase transfer catalysis and biological studies [3, 4]. In recent years, the chemistry of transition metal ion-based complexes of ligands has attracted enormous interest in the field of coordination chemistry [5–7]. Many transition metals prompted Schiff base complexes have been reported to perform the excellent catalytic activity in various homogeneous and heterogeneous reactions [8]. However, these Schiff base complexes generally suffer from certain drawbacks including instability, expensive and tedious purifi
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