Copyright (c) 2025 Vasupavani D, Vaikuntarao L
This work is licensed under a Creative Commons Attribution 4.0 International License.
Iron Oxide Nanoparticles-Catalyzed Oxidative Cyclization for Synthesis of 2-Substituted Quinazolinones and Benzimidazoles
Corresponding Author(s) : D.V.R. Vasupavani
Asian Journal of Chemistry,
Vol. 37 No. 2 (2025): Vol 37 Issue 2, 2025
Abstract
Hydrothermally synthesized nanoscale iron(III) oxide (Fe2O3) particles catalyzed the one-pot synthesis of 2-aryl-substituted quinazolinones and benzimidazoles from 2-aminobenzamide and 1,2-diaminoarenes with arylmethane via oxidative cyclization. A key advantage of this method is the use of water as a green solvent, enabling the efficient production of quinazolinones and benzimidazoles in excellent yields, without the need for a base, ligand, or toxic metals. This method is a successful and eco-friendly protocol for synthesizing a wide variety of heterocyclic compounds, and the high surface reactivity of the catalyst is probably a contributing factor.
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K.W. Bentley, Nat. Prod. Rep., 23, 444 (2006); https://doi.org/10.1039/B509523A
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J.B. Koepfli, J.A. Brockman Jr. and J. Moffat, J. Am. Chem. Soc., 72, 3323 (1950); https://doi.org/10.1021/ja01163a555
L.C.R. Carvalho, E. Fernandes and M.M.B. Marques, Chemistry, 17, 12544 (2011); https://doi.org/10.1002/chem.201101508
B.S. Kuarm, Y.T. Reddy, J.V. Madhav, P.A. Crooks and B. Rajitha, Bioorg. Med. Chem. Lett., 21, 524 (2011); https://doi.org/10.1016/j.bmcl.2010.10.082
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T.B. Nguyen, L. Ermolenko and A. Al-Mourabit, J. Am. Chem. Soc., 135, 118 (2013); https://doi.org/10.1021/ja311780a
H. Baars, A. Beyer, S.V. Kohlhepp and C. Bolm, Org. Lett., 16, 536 (2014); https://doi.org/10.1021/ol403414v
R.K. Kumar and T. Punniyamurthy, RSC Adv., 2, 4616 (2012); https://doi.org/10.1039/c2ra20328f
N.T. Chung, V.C. Dung and D.X. Duc, RSC Adv., 13, 32734 (2023); https://doi.org/10.1039/D3RA05960J
N.Y. Kim and C.H. Cheon, Tetrahedron Lett., 55, 2340 (2014); https://doi.org/10.1016/j.tetlet.2014.02.065
D. Mahesh, P. Sadhu and T. Punniyamurthy, J. Org. Chem., 81, 3227 (2016); https://doi.org/10.1021/acs.joc.6b00186
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G. Evano, N. Blanchard and M. Toumi, Chem. Rev., 108, 3054 (2008); https://doi.org/10.1021/cr8002505
J.P. Corbet and G. Mignani, Chem. Rev., 106, 2651 (2006); https://doi.org/10.1021/cr0505268
A. Correa, O. García Mancheño and C. Bolm, Chem. Soc. Rev., 37, 1108 (2008); https://doi.org/10.1039/b801794h
S. Würtz and F. Glorius, Acc. Chem. Res., 41, 1523 (2008); https://doi.org/10.1021/ar8000876
Y. Jun, J. Seo, S. Oh and J. Cheon, Coord. Chem. Rev., 249, 1766 (2005); https://doi.org/10.1016/j.ccr.2004.12.008
P.D. Burton, E.J. Peterson, T.J. Boyle and A.K. Datye, Catal. Lett., 139, 26 (2010); https://doi.org/10.1007/s10562-010-0405-1
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O.Yu. Slabko and V.A. Kaminskii, Russ. J. Org. Chem., 55, 152 (2019); https://doi.org/10.1134/S1070428019020052
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S.M. Botsa and K. Basavaiah, Sci. Rep., 10, 14080 (2020); https://doi.org/10.1038/s41598-020-70194-9
G.S. Sree, K.V.B. Ranjitha, B.J.M. Reddy, B.S. Mohan and C.R. Kant, Inorg. Chem. Commun., 155, 111054 (2023); https://doi.org/10.1016/j.inoche.2023.111054
J.R. Sunkara and S.M. Botsa, Chem. Africa, 2, 635 (2019); https://doi.org/10.1007/s42250-019-00086-7
J. Feng, M.F. Lv, G.P. Lu and C. Cai, Org. Chem. Front., 2, 60 (2015); https://doi.org/10.1039/C4QO00293H