A novel Cu complex coated on hercynite magnetic nanoparticles as an efficient and recoverable nanocatalyst for the selective synthesis of tetrazoles
Source abstract
Abstract
In this study, hercynite magnetic nanoparticles (FeAl2O4 MNPs) were synthesized using commercially available materials, including FeCl2.4H2O and Al(NO3)3·9H2O. The surface of FeAl2O4 MNPs was encapsulated using silica and then modified by 3-aminooropropyltrimtoxysilane (APTMS). The modified FeAl2O4 MNPs were further functionalized with tris(hydroxymethyl)amino methane (THAM). Finally, a new copper complex of THAM was stabilized on the surface of functionalized FeAl2O4 MNPs (Cu-THAM@SiO2@FeAl2O4) as a novel, magnetically recoverable, practical, and selective nanocatalyst. The nanocatalyst was characterized using a range of techniques, including atomic absorption spectroscopy (AAS), vibrating-sample magnetometer (VSM), X-ray-mapping analysis, energy dispersive X-ray spectroscopy (EDS), scanning electron microscope (SEM), thermogravimetric analysis (TGA), derivative thermogravimetric (DTG), Fourier transform infrared spectroscopy (FT-IR), and X-ray diffraction (XRD) techniques. The results showed that Cu-THAM@SiO2@FeAl2O4 nanocatalyst was highly efficiency, good selectivity, and excellent reusability in the synthesis of tetrazole derivatives through [3 + 2] cycloaddition of sodium azide (NaN3) with organic nitrile derivatives. Graphical Abstract
Source: expertdata · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Synthesis of Tetrazole Derivatives · Multicomponent Synthesis of Heterocycles · Microwave-Assisted Synthesis and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (56)
Show source-provided references
1. Schnitzer T, Vantomme G (2020) Synthesis of complex molecular systems—the foreseen role of organic chemists. ACS Cent Sci 6:2060–207010.1021/acscentsci.0c00974 ↗
2. Lasso JD, Castillo-Pazos DJ, Li CJ (2021) Green chemistry meets medicinal chemistry: a perspective on modern metal-free late-stage functionalization reactions. Chem Soc Rev 50:10955–1098210.1039/D1CS00380A ↗
3. Batista, VF, Pinto, GA DC, Silva, AM (2020) Iron a worthy contender in metal carbene chemistry. ACS Catal 10: 10096–1011610.1021/acscatal.0c02776 ↗
4. Khatoon H, Abdulmalek E (2021) A focused review of synthetic applications of Lawesson’s reagent in organic synthesis. Molecules 26:693710.3390/molecules26226937 ↗
5. Tiburcio E, Greco R, Mon M, Ballesteros-Soberanas J, Ferrando-Soria J, López-Haro M, Pardo E (2021) Soluble/MOF-supported palladium single atoms catalyze the ligand-, additive-, and solvent-free aerobic oxidation of benzyl alcohols to benzoic acids. J Am Chem Soc 143:2581–259210.1021/jacs.0c12367 ↗
6. Carné-Sánchez A, Craig GA, Larpent P, Guillerm V, Urayama K, Maspoch D, Furukawa S (2019) A coordinative solubilizer method to fabricate soft porous materials from insoluble metal–organic polyhedra. Angew Chem 131:6413–641610.1002/ange.201901668 ↗
7. Sankar M, He Q, Engel RV, Sainna MA, Logsdail AJ, Roldan A, Hutchings GJ (2020) Role of the support in gold-containing nanoparticles as heterogeneous catalysts. Chem Rev 120:3890–393810.1021/acs.chemrev.9b00662 ↗
8. Zhang Q, Yang X, Guan J (2019) Applications of magnetic nanomaterials in heterogeneous catalysis. ACS Appl Nano Mater 2:4681–469710.1021/acsanm.9b00976 ↗
9. Ghorbani-Choghamarani A, Norouzi M (2016) Synthesis and characterization of ionic liquid immobilized on magnetic nanoparticles: a recyclable heterogeneous organocatalyst for the acetylation of alcohols. J Magn Magn Mater 401:832–84010.1016/j.jmmm.2015.10.044 ↗
10. Singh G, Singh A, Satija P, González-Silvera D, Espinosa-Ruíz C, Esteban MA (2021) Organosilanes and their magnetic nanoparticles as naked eye red emissive sensors for Ag+ ions and potent anti-oxidants. New J Chem 45:5517–552510.1039/D1NJ00242B ↗
11. Wu K, Su D, Liu J, Saha R, Wang JP (2019) Magnetic nanoparticles in nanomedicine: a review of recent advances. Nanotechnology 30:50200310.1088/1361-6528/ab4241 ↗
12. Angelopoulou A, Kolokithas-Ntoukas A, Fytas C, Avgoustakis K (2019) Folic acid-functionalized, condensed magnetic nanoparticles for targeted delivery of doxorubicin to tumor cancer cells overexpressing the folate receptor. ACS Omega 4:22214–2222710.1021/acsomega.9b03594 ↗
13. Gloag L, Mehdipour M, Chen D, Tilley RD, Gooding JJ (2019) Advances in the application of magnetic nanoparticles for sensing. Adv Mater 31:190438510.1002/adma.201904385 ↗
14. Martins PM, Lima AC, Ribeiro S, Lanceros-Mendez S, Martins P (2021) Magnetic nanoparticles for biomedical applications: from the soul of the earth to the deep history of ourselves. ACS Appl Bio Mater 4:5839–587010.1021/acsabm.1c00440 ↗
15. Norouzi M, Ghorbani-Choghamarani A, Nikoorazm M (2016) Heterogeneous Cu(II)/L-His@Fe3O4 nanocatalyst: a novel, efficient and magnetically-recoverable catalyst for organic transformations in green solvents. RSC adv 6:92387–9240110.1039/C6RA19776K ↗
16. Ghorbani-Choghamarani A, Norouzi M (2016) Palladium supported on modified magnetic nanoparticles: a phosphine-free and heterogeneous catalyst for Suzuki and Stille reactions. Appl Organometal Chem 30:140–14710.1002/aoc.3409 ↗
17. Ghorbani-Choghamarani A, Norouzi M (2016) Suzuki Stille and Heck cross-coupling reactions catalyzed by Fe 3O4@ PTA–Pd as a recyclable and efficient nanocatalyst in green solvents. New J Chem 40:6299–630710.1039/C6NJ00088F ↗
18. Darwesh OM, Matter IA, Eida MF (2019) Development of peroxidase enzyme immobilized magnetic nanoparticles for bioremediation of textile wastewater dye. J Environ Chem Eng 7:10280510.1016/j.jece.2018.11.049 ↗
19. Ma Z, Mohapatra J, Wei K, Liu JP, Sun S (2021) Magnetic nanoparticles: synthesis, anisotropy, and applications. Chem Rev 123:3904–394310.1021/acs.chemrev.1c00860 ↗
20. Shasha C, Krishnan KM (2021) Nonequilibrium dynamics of magnetic nanoparticles with applications in biomedicine. Adv Mater 33:190413110.1002/adma.201904131 ↗
21. Zhang Q, Yang X, Guan J (2019) Applications of magnetic nanomaterials in heterogeneous catalysis. ACS Appl Nano Mater 2:4681–469710.1021/acsanm.9b00976 ↗
22. Mohammadi M, Ghorbani-Choghamarani A (2022) Hercynite silica sulfuric acid: a novel inorganic sulfurous solid acid catalyst for one-pot cascade organic transformations. RSC adv 12:26023–2604110.1039/D2RA03481F ↗
23. Kazemi S, Alavi SM, Rezaei M, Akbari E (2024) Preparation of the NiO/FeAl2O4 nanopowders and their application in CH4 thermocatalytic decomposition to produce high purity of hydrogen: Optimization of the synthesis parameters using Taguchi design of experiment. Int J Hydrog Energy 51:1429–4910.1016/j.ijhydene.2023.07.332 ↗
24. Mohammadi M, Ghorbani-Choghamarani A (2022) A novel hercynite-supported tetradentate Schiff base complex of manganese catalyzed one-pot annulation reactions. Appl Organometal Chem 36:e690510.1002/aoc.6905 ↗
25. Millican SL, Clary JM, Musgrave CB, Lany S (2022) Redox defect thermochemistry of FeAl2O4 hercynite in water splitting from first-principles methods. Chem Mater 34:519–52810.1021/acs.chemmater.1c01049 ↗
26. Ishihara K, Shioiri T, Matsugi M (2020) An expeditious approach to tetrazoles from amides utilizing phosphorazidates. Org Lett 22:6244–624710.1021/acs.orglett.0c01890 ↗
27. Dhiman N, Kaur K, Jaitak V (2020) Tetrazoles as anticancer agents: a review on synthetic strategies, mechanism of action and SAR studies. Bioorg Med Chem 28:11559910.1016/j.bmc.2020.115599 ↗
28. Carpentier F, Felpin FX, Zammattio F, Le Grognec E (2020) Synthesis of 5-substituted 1H-tetrazoles from nitriles by continuous flow: application to the synthesis of valsartan. Org Process Res Dev 24:752–76110.1021/acs.oprd.9b00526 ↗
29. Nasrollahzadeh M, Nezafat Z, Bidgoli NSS, Shafiei N (2021) Use of tetrazoles in catalysis and energetic applications: recent developments. Mol Catal 513:11178810.1016/j.mcat.2021.111788 ↗
30. Halder M, Islam MM, Singh P, Singha Roy A, Islam SM, Sen K (2018) Sustainable generation of Ni(OH)2 nanoparticles for the green synthesis of 5-substituted 1H-tetrazoles: a competent turn on fluorescence sensing of H2O2. ACS Omega 3:8169–818010.1021/acsomega.8b01081 ↗
31. Florindo PR, Costa PJ, Piedade MFM, Robalo MP (2017) pH-switchability and second-order nonlinear optical properties of monocyclopentadienylruthenium(II)/iron(II) tetrazoles/tetrazolates: synthesis, characterization, and time-dependent density functional theory calculations. Inorg Chem 56:6849–686310.1021/acs.inorgchem.7b00138 ↗
32. Ilyushin MA, Tselinsky IV, Shugalei IV (2012) Environmentally friendly energetic materials for initiation devices. CeCent Eur J Energ Mater 9:293–327
33. Liu CC, Qiao B, Qu LB, Zhang T, Li SJ, Lan Y (2022) The regioselectivity of the sulfonylation of tetrazoles: a theoretical view. Org Chem Front 9:4009–401510.1039/D2QO00797E ↗
34. Khodamorady M, Ghobadi N, Bahrami K (2021) Homoselective synthesis of 5-substituted 1H-tetrazoles and one-pot synthesis of 2, 4, 5-trisubstuted imidazole compounds using BNPs@SiO2-TPPTSA as a stable and new reusable nanocatalyst. Appl Organomet Chem 35:e614410.1002/aoc.6144 ↗
35. Neochoritis CG, Zhao T, Dömling A (2019) Tetrazoles via multicomponent reactions. Chem Rev 119:1970–204210.1021/acs.chemrev.8b00564 ↗
36. Leyva-Ramos S, Cardoso-Ortiz J (2021) Recent developments in the synthesis of tetrazoles and their pharmacological relevance. Curr Org Chem 25:388–40310.2174/18755348MTEyoMzEFz ↗
37. Swami S, Sahu SN, Shrivastava R (2021) Nanomaterial catalyzed green synthesis of tetrazoles and its derivatives: a review on recent advancements. RSC adv 11:39058–3908610.1039/D1RA05955F ↗
38. Sharifzadeh Z, Abedi S, Morsali A (2014) Fabrication of novel multi-morphological tetrazole-based infinite coordination polymers; transformation studies and their calcination to mineral zinc oxide nano- and microarchitectures. J Mater Chem A 2:4803–481010.1039/c3ta14904h ↗
39. Rama V, Kanagaraj K, Pitchumani K (2011) Syntheses of 5-substituted 1H-tetrazoles catalyzed by reusable CoY zeolite. J Org Chem 76:9090–909510.1021/jo201261w ↗
40. Aridoss G, Laali KK (2011) Highly efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by Cu–Zn alloy nanopowder, conversion into 1,5- and 2,5-disubstituted tetrazoles, and synthesis and NMR studies of new tetrazolium ionic liquids. Eur J Org Chem 2011:6343–635510.1002/ejoc.201100957 ↗
41. Tienan J, Kitahara F, Kamijo S, Yamamoto Y (2008) Synthesis of 5-substituted 1H-tetrazoles by the copper-catalyzed [3+ 2] cycloaddition of nitriles and trimethylsilyl azide. Chem Asian J 8–9:1575–1580
42. Tienan J, Kitahara F, Kamijo S, Yamamoto Y (2008) Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+ 2] cycloaddition of nitriles and trimethylsilyl azide. Tetrahedron Lett 49:2824–282710.1016/j.tetlet.2008.02.115 ↗
43. Ghorbani-Choghamarani A, Shiri L, Azadi G (2016) The first report on the eco-friendly synthesis of 5-substituted 1H-tetrazoles in PEG catalyzed by Cu(II) immobilized on Fe3O4@SiO2@L-arginine as a novel, recyclable and non-corrosive catalyst. RSC Adv 6:32653–3266010.1039/C6RA03023H ↗
44. Mittal R, Bladin J, Bamberger E, De Gruyter P, Butler R, Katritzky A, Rees C, Scriven E, Jursic B, Le Blanc B, Koldobskii G (2019) Recent advances in the synthesis of 5-substituted 1H-tetrazoles: A complete survey (2013–2018). Synthesis 20:3765–3783
45. AbbasiTyula Y, Moradi P, Nikoorazm M (2023) A new neodymium complex on boehmite nanoparticles with 1,3-bis(pyridine-3-ylmethyl)thiourea as a practical and reusable nanocatalyst for the chemoselective synthesis of tetrazoles. ChemistrySelect 8:e20230167410.1002/slct.202301674 ↗
46. Ghorbani-Choghamarani A, Aghavandi H, Talebi SM (2022) A new copper-supported zinc ferrite as a heterogeneous magnetic nanocatalyst for the synthesis of bis (pyrazolyl) methanes and oxidation of sulfides. Sci Rep 12:2077510.1038/s41598-022-25170-w ↗
47. Tahmasbi B, Ghorbani-Choghamarani A (2019) Magnetic MCM-41 nanoparticles as a support for the immobilization of a palladium organometallic catalyst and its application in C-C coupling reactions. New J Chem 43:14485–1450110.1039/C9NJ02727K ↗
48. Norouzi M, Moradi P (2023) A new copper complex on functionalized magnetic biochar nano-sized materials as sustainable heterogeneous catalysts for C-O bond formation in the natural deep eutectic solvent. Biomass Convers Biorefin 1–13. https://doi.org/10.1007/s13399-023-05163-z10.1007/s13399-023-05163-z ↗
49. Kumar Prajapti S, Nagarsenkar A, NagendraBabu B (2014) An efficient synthesis of 5-substituted 1H-tetrazoles via B (C6F5) 3 catalyzed [3+ 2] cycloaddition of nitriles and sodium azide. Tetrahedron Lett 55:3507–351010.1016/j.tetlet.2014.04.089 ↗
50. Dehghani F, Sardarian AR, Esmaeilpour M (2013) Salen complex of Cu(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: an efficient and recyclable catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles. J Organomet Chem 743:87–9610.1016/j.jorganchem.2013.06.019 ↗
51. Qi G, Liu W, Bei Z (2011) Fe3O4/ZnS hollow nanospheres: a highly efficient magnetic heterogeneous catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide. Chin J Chem 29:131–13410.1002/cjoc.201190039 ↗
52. Lang L, Zhou H, Xue M, Wang X, Xu Z (2013) Mesoporous ZnS hollow spheres-catalyzed synthesis of 5-substituted 1H-tetrazoles. Mater Lett 106:443–44610.1016/j.matlet.2013.05.067 ↗
53. Sreedhar B, Suresh Kumar A, Yada D (2011) CuFe2O4 nanoparticles: a magnetically recoverable and reusable catalyst for the synthesis of 5-substituted 1H-tetrazoles. Tetrahedron Lett 52:3565–356910.1016/j.tetlet.2011.04.094 ↗
54. Moradi P, Hajjami M, Tahmasbi B (2020) Fabricated copper catalyst on biochar nanoparticles for the synthesis of tetrazoles as antimicrobial agents. Polyhedron 175:11416910.1016/j.poly.2019.114169 ↗
55. Norouzi M, Noormoradi N, Mohammadi M (2023) Nanomagnetic tetraaza (N4 donor) macrocyclic Schiff base complex of copper (ii): synthesis, characterizations, and its catalytic application in Click reactions. Nanoscale Adv 23:6594–660510.1039/D3NA00580A ↗
56. Norouzi M, Moradi P, Khanmoradi M (2023) Aluminium-based ionic liquid grafted on biochar as a heterogeneous catalyst for the selective synthesis of tetrazole and 2,3-dihydroquinazolin 4(1H)-one derivatives. RSC adv 13:35569–3558210.1039/D3RA06440A ↗