Methionine-Coated Fe 3 O 4 Nanoparticles: An Efficient and Reusable Nanomagnetic Catalyst for the Synthesis of 5-Substit
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ethionine-Coated Fe3O4 Nanoparticles: An Efficient and Reusable Nanomagnetic Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles A. Karimiana,*, M. Namvar-Mhabouba, and R. Abbasia a
Department of Chemistry, Faculty of Sciences, University of Gonabad, Gonabad, 9691957678 Iran *e-mail: [email protected] Received March 26, 2020; revised April 4, 2020; accepted April 16, 2020
Abstract—Methionine-coated Fe3O4 nanoparticles, a magnetically reusable and environmentally friendly heterogeneous catalyst, was synthesized. The new catalyst was characterized by FT-IR spectra, XRD, SEM, and EDX analysis and was used to catalyze the cycloaddition of nitriles and sodium azide in DMSO at 120°C to give the corresponding 5-substituted 1H-tetrazoles. Methionine-coated Fe3O4 nanoparticles proved to be highly efficient for this organic reaction. The catalyst can be easily separated and reused several times without loss of activity. The proposed procedure also offers several benefits such as quick reaction, high yields, clean process, low-cost heterogeneous catalyst, low loading of catalyst, and simple operation. Keywords: tetrazoles, methionine, heterogeneous catalyst, magnetically recoverable catalyst
DOI: 10.1134/S1070428020090237 INTRODUCTION Tetrazoles constitute an essential class of heterocyclic compounds that have gained much interest due to wide range of their use in medicine [1–4]. For example, tetrazole ring is present in various biologically active compounds such as antibiotics, antiviral (i.e., HIV) [5], antiplatelet [6], cardiazol [7], and “sartan” family drugs. Heterocyclic compounds containing a tetrazole moiety are also used in materials science [8], coordination chemistry [9], and as plant growth regulators in agriculture [10]. Accordingly, it is important to search for efficient methods of synthesis of 5-substituted 1H-tetrazoles. The commonly employed method involves the [3+2]cycloaddition reaction between nitriles and azides. Other routes for the synthesis of tetrazoles include the use of thioamides, imidoyl chlorides, oximes, heterocumulenes, ketones, amines, alkenes, or isocyanides as starting materials in the presence of azide ion source [5]. These procedures utilize numerous catalysts such as Pd catalysts [11], CuI [12], Cu2O [13], ZnO [14], CuFe 2 O 4 [15], CuSO 4 ·5H 2 O [16], Fe(OAc) 2 [17], Fe 3O 4@chitin [18], Cu-MCM-41 [19], InCl 3 [20], AgNO3 [21], FeCl3/SiO2 [22], ZnCl2 [23], ZrOCl2· 8H2O [24], B(C6H5)3 [25], DPPA/DBU [26], BaWO4
[27], Ln(OTf) 3 /SiO 2 [28], Zn–Cu alloy [29], I2/NaHSO4/SiO2 [30], mesoporous ZnS nanospheres [31], COY zeolite [32], cuttlebone [33], and P2O5 [34]. Recently, a few research teams have also used microwave irradiation to shorten the reaction time [35–39]. Based on the facts mentioned above and in continuation of our research program on the synthesis of heterogeneous catalysts and heterocyclic compounds [40–44], we now report the synthesis of methioninecoated Fe3O4 nanoparticles as a novel, efficient, and recyclable heterogeneous catalyst with high catalytic activity
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