The Effect Study of Various Parameters on the Synthesis of Benzoxazole Derivatives Utilizing Cadmium Oxide Nanoparticles

Year 2024, Volume: 11 Issue: 1, 391 - 402, 04.02.2024

Asmaa Abdullah , Abdull Jabar Attia , Sergei Shtykov

Abstract

Due to its straightforward approach, the co-precipitation technique for producing nanomaterials has gained popularity over time. In this study, we employed cadmium nitrate to synthesize cadmium oxide nanomaterials (CdO NPs). The morphology and size of the synthesized CdO NPs were determined using Scanning Electron Microscopy (SEM) and Atomic Force Microscopy (AFM) respectively. To find the functional groups that are present in the nanoparticles and are involved in their decrease and stabilization, a Fourier Transform Infrared Spectroscopy (FTIR) study was carried out. Additionally, X-ray diffraction analysis (XRD) was employed to confirm the crystalline nature of the NPs. By utilizing the synthesized catalyst CdO NPs, we successfully synthesized benzoxazole derivatives with improved yields by reacting o-amino phenol with various aldehydes, achieving yields of 90-93%. The structures of the synthesized molecules were characterized using NMR and FTIR spectroscopy. Noteworthy advantages of this method include its short reaction time, high product yields, and the catalyst's recyclability.

Keywords

Benzoxazole, Cadmium oxide NPs, Nanoparticles, co-precipitation.

Thanks

The authors extend their thanks to Al-Mustansiriyah University, the College of Science, and the laboratories of the Department of Chemistry for their support in terms of equipment and chemical materials.

References

• 1. Mahesh S, Narasaiah BP, Balaji G. Fabrication of titanium dioxide nanoparticles using sunflower leaf extract and their applications towards the synthesis and biological evaluation of some novel phenanthro imidazole derivatives. Biointerface Research in Applied Chemistry. 2022;12:3372–89. Available from: <URL>.
• 2. Skheel AZ, Hlail Jaduaa M, Abd AN. Green synthesis of cadmium oxide nanoparticles for biomedical applications (antibacterial, and anticancer activities). Materials Today: Proceedings. 2021;45:5793–9. Available from: <URL>.
• 3. Ranjithkumar R, Albert Irudayaraj A, Jayakumar G, Dhayal Raj A, Karthick S, Vinayagamoorthy R. Synthesis and Properties of CdO and Fe doped CdO Nanoparticles. Materials Today: Proceedings. 2016;3(6):1378–82. Available from: <URL>.
• 4. Mostafa AM, Yousef SA, Eisa WH, Ewaida MA, Al-Ashkar EA. Synthesis of cadmium oxide nanoparticles by pulsed laser ablation in liquid environment. Optik. 2017 Sep;144:679–84. Available from: <URL>.
• 5. Giribabu K, Suresh R, Vijayalakshmi L, Stephen A, Narayanan V. Synthesis of Cadmium Oxide and its Electrochemical Detection of Pollutants. Advanced Materials Research. 2013 Mar;678:369–72. Available from: <URL>.
• 6. Reza Khayati G, Dalvand H, Darezereshki E, Irannejad A. A facile method to synthesis of CdO nanoparticles from spent Ni–Cd batteries. Materials Letters. 2014 Jan;115:272–4. Available from: <URL>.
• 7. Gorepatil PB, Mane YD, Ingle VS. Zirconyl (IV) Nitrate as Efficient and Reusable Solid Lewis Acid Catalyst for the Synthesis of Benzimidazole Derivatives. Journal of Chemistry. 2013;2013:1–7. Available from: <URL>.
• 8. Mohamed Ahmed MS, Kobayashi K, Mori A. One-Pot Construction of Pyrazoles and Isoxazoles with Palladium-Catalyzed Four-Component Coupling. Org Lett. 2005 Sep 1;7(20):4487–9. Available from: <URL>.
• 9. Kidwai M, Poddar R, Diwaniyan S, Kuhad RC. Laccase from Basidiomycetous Fungus Catalyzes the Synthesis of Substituted 5‐Deaza‐10‐oxaflavins via a Domino Reaction. Adv Synth Catal. 2009 Mar;351(4):589–95. Available from: <URL>.
• 10. Ahmed A, Majeed I, Asaad N, Ahmed R, Kamil G, Abdul Rahman S. Some 3,4,5-Trisubstituted-1,2,4-triazole Synthesis, Antimicrobial Activity, and Molecular Docking Studies. Egypt J Chem. 2021 Sep 23;65(3):395–401. Available from: <URL>.
• 11. Yalçin İ, Ören İ, Şener E, Akin A, Uçartürk N. The synthesis and the structure-activity relationships of some substituted benzoxazoles, oxazolo(4,5-b)pyridines, benzothiazoles and benzimidazoles as antimicrobial agents. European Journal of Medicinal Chemistry. 1992 Jun;27(4):401–6. Available from: <URL>.
• 12. Díez-Martin D, Kotecha NR, Ley SV, Mantegani S, Menéndez JC, Organ HM, et al. Total synthesis of the ionophore antibiotic CP-61,405 (routiennocin). Tetrahedron. 1992 Jan;48(37):7899–938. Available from: <URL>.
• 13. Abdelgawad MA, Al-Sanea MM, Zaki MA, Mohamed EIA, Khan SI, Tekwani BL, et al. New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation. Ramalho TC, editor. Journal of Chemistry. 2021 Mar 3;2021:1–11. Available from: <URL>.
• 14. Oren I, Temiz O, Yalçin I, Sener E, Akin A, Uçartürk N. Synthesis and microbiological activity of 5(or 6)-methyl-2-substituted benzoxazole and benzimidazole derivatives. Arzneimittel-forschung. 1997 Dec;47(12):1393–7. Available from: <URL>.
• 15. Al-Sanea M, Abdelazem A, Park B, Yoo K, Sim T, Kwon Y, et al. ROS1 kinase inhibitors for molecular-targeted therapies. Current medicinal chemistry. 2016;23(2):142–60.
• 16. Alsayed SSR, Elshemy HAH, Abdelgawad MA, Abdel-Latif MS, Abdellatif KRA. Design, synthesis and biological screening of some novel celecoxib and etoricoxib analogs with promising COX-2 selectivity, anti-inflammatory activity and gastric safety profile. Bioorganic Chemistry. 2017 Feb;70:173–83. Available from: <URL>.
• 17. Pinar A, Yurdakul P, Yildiz I, Temiz-Arpaci O, Acan NL, Aki-Sener E, et al. Some fused heterocyclic compounds as eukaryotic topoisomerase II inhibitors. Biochemical and Biophysical Research Communications. 2004 Apr;317(2):670–4. Available from: <URL>.
• 18. Temiz-Arpaci O, Tekiner-Gulbas B, Yildiz I, Aki-Sener E, Yalcin I. 3D-QSAR analysis on benzazole derivatives as eukaryotic topoisomerase II inhibitors by using comparative molecular field analysis method. Bioorganic & Medicinal Chemistry. 2005 Dec;13(23):6354–9. Available from: <URL>.
• 19. Tekiner-Gulbas B, Temiz-Arpaci O, Yildiz I, Aki-Sener E, Yalcin I. 3D-QSAR study on heterocyclic topoisomerase II inhibitors using CoMSIA. SAR and QSAR in Environmental Research. 2006 Apr;17(2):121–32. Available from: <URL>.
• 20. Lage H, Aki‐Sener E, Yalcin I. High antineoplastic activity of new heterocyclic compounds in cancer cells with resistance against classical DNA topoisomerase II‐targeting drugs. Intl Journal of Cancer. 2006 Jul;119(1):213–20. Available from: <URL>.
• 21. Abdelgawad MA, Belal A, Ahmed OM. Synthesis, molecular docking studies and cytotoxic screening of certain novel thiazolidinone derivatives substituted with benzothiazole or benzoxazole. Journal of Chemical and Pharmaceutical Research. 2013;5(2):318–27.
• 22. Abdellatif KRA, Abdelall EKA, Abdelgawad MA, Amin DME, Omar HA. Design, synthesis and biological evaluation of new 4-(4-substituted-anilino)quinoline derivatives as anticancer agents. Med Chem Res. 2017 May;26(5):929–39. Available from: <URL>.
• 23. Kandeel MM, Ali SM, ElALL E, Abdelgawad MA, Lamie PF. Synthesis and antitumor activity of novel pyrazolo [3, 4-d] pyrimidines and related heterocycles. Der Pharma Chemica. 2012;4:1704–15.
• 24. Abdellatif KRA, Abdelgawad MA, Labib MB, Zidan TH. Synthesis and Biological Evaluation of New Diarylpyrazole and Triarylimidazoline Derivatives as Selective COX‐2 Inhibitors. Archiv der Pharmazie. 2017 Aug;350(8):1600386. Available from: <URL>.
• 25. Abdellatif KRA, Abdelgawad MA, Elshemy HAH, Alsayed SSR, Kamel G. Synthesis and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives possessing an aminosulphonyl pharmacophore. Arch Pharm Res. 2015 Nov;38(11):1932–42. Available from: <URL>.
• 26. Tipparaju SK, Joyasawal S, Pieroni M, Kaiser M, Brun R, Kozikowski AP. In Pursuit of Natural Product Leads: Synthesis and Biological Evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxylic acid (A-33853) and Its Analogues: Discovery of N -(2-Benzoxazol-2-ylphenyl)benzamides as Novel Antileishmanial Chemotypes. J Med Chem. 2008 Dec 11;51(23):7344–7. Available from: <URL>.
• 27. Akbay A, Ören İi, Temiz-Arpacı Ö, Akı-Sener E, Yalcçın I. Synthesis and HIV-1 Reverse Transcriptase Inhibitor Activity of Some 2,5,6-Substituted Benzoxazole, Benzimidazole, Benzothiazole and Oxazolo(4,5-b)pyridine Derivatives. Arzneimittel-forschung. 2011 Dec 25;53(04):266–71. Available from: <URL>.
• 28. Plemper RK, Erlandson KJ, Lakdawala AS, Sun A, Prussia A, Boonsombat J, et al. A target site for template-based design of measles virus entry inhibitors. Proceedings of the National Academy of Sciences of the Unitedt States of America. 2004 Apr 13;101(15):5628–33. Available from: <URL>.
• 29. Yildiz‐Oren I, Tekiner‐Gulbas B, Yalcin I, Temiz‐Arpaci O, Akı‐Sener E, Altanlar N. Synthesis and Antimicrobial Activity of New 2‐[p‐Substituted‐benzyl]‐5‐[substituted‐carbonylamino] benzoxazoles. Archiv der Pharmazie. 2004 Jul;337(7):402–10. Available from: <URL>.
• 30. Yoshida S, Shiokawa S, Kawano K ichi, Ito T, Murakami H, Suzuki H, et al. Orally Active Benzoxazole Derivative as 5-HT 3 Receptor Partial Agonist for Treatment of Diarrhea-Predominant Irritable Bowel Syndrome. J Med Chem. 2005 Nov 1;48(22):7075–9. Available from: <URL>.
• 31. Chen TR. Synthesis and characterization of cyclometalated iridium(III) complexes containing benzoxazole derivatives and different ancillary ligands. Journal of Organometallic Chemistry. 2008 Sep;693(19):3117–30. Available from: <URL>.
• 32. Varma RS, Kumar D. Manganese triacetate oxidation of phenolic schiffs bases: Synthesis of 2‐arylbenzoxazoles. Journal of Heterocyclic Chem. 1998 Nov;35(6):1539–40. Available from: <URL>.
• 33. Chang J, Zhao K, Pan S. Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases—a solution-phase strategy for library synthesis. Tetrahedron Letters. 2002 Feb;43(6):951–4. Available from: <URL>.
• 34. Nakagawa K, Onoue H, Sugita J. Oxidation with Nickel Peroxide. IV. The Preparation of Benzoxazoles from Schiff’s Bases. Chem Pharm Bull. 1964;12(10):1135–8. Available from: <URL>.
• 35. Iranpoor N, Baltork IM. Mild, Efficient and Selective Opening of Epoxides with Alcohols Catalyzed by Ceric(IV) Ammonium Nitrate. Synthetic Communications. 1990 Sep;20(18):2789–97. Available from: <URL>.
• 36. Praveen C, Kumar KH, Muralidharan D, Perumal PT. Oxidative cyclization of thiophenolic and phenolic Schiff’s bases promoted by PCC: a new oxidant for 2-substituted benzothiazoles and benzoxazoles. Tetrahedron. 2008 Mar;64(10):2369–74. Available from: <URL>.
• 37. Bose D, Idrees Mohd. Dess-Martin Periodinane Mediated Intramolecular Cyclization of Phenolic Azomethines: A Solution-Phase Strategy toward Benzoxazoles and Benzothiazoles. Synthesis. 2010 Feb;2010(03):398–402. Available from: <URL>.
• 38. Srivastava RG, Venkataramani PS. Barium Manganate Oxidation in Organic Synthesis: Part III: Oxidation of Schiff’S Bases to Benzimidazoles Benzoxazoles and Benzthiazoles. Synthetic Communications. 1988 Sep;18(13):1537–44. Available from: <URL>.
• 39. Patil MR, Bhanushali JT, Nagaraja BM, Keri RS. TiO 2 ZrO 2 composite: Synthesis, characterization and application as a facile, expeditious and recyclable catalyst for the synthesis of 2-aryl substituted benzoxazole derivatives. Comptes Rendus Chimie. 2018 Mar;21(3–4):399–407. Available from: <URL>.
• 40. Talodthaisong C, Plaeyao K, Mongseetong C, Boonta W, Srichaiyapol O, Patramanon R, et al. The Decoration of ZnO Nanoparticles by Gamma Aminobutyric Acid, Curcumin Derivative and Silver Nanoparticles: Synthesis, Characterization and Antibacterial Evaluation. Nanomaterials. 2021 Feb 9;11(2):442. Available from: <URL>.
• 41. Nguyen LHT, Nguyen TT, Nguyen HL, Doan TLH, Tran PH. A new superacid hafnium-based metal–organic framework as a highly active heterogeneous catalyst for the synthesis of benzoxazoles under solvent-free conditions. Catalysis Science & Technology. 2017;7(19):4346–50. Available from: <URL>.
• 42. Bhat R, Karhale S, Arde S, Helavi V. Acacia concinna pod catalyzed synthesis of 2-arylbenzothia/(oxa) zole derivatives. Iranian Journal of Catalysis. 2019;9(2):173–9.
• 43. Chikhale RV, Pant AM, Menghani SS, Wadibhasme PG, Khedekar PB. Facile and efficient synthesis of benzoxazole derivatives using novel catalytic activity of PEG-SO 3 H. Arabian Journal of Chemistry. 2017 Jul;10(5):715–25. Available from: <URL>.
• 44. Mazaheritehrani M, Asghari J, Orimi RL, Pahlavan S. Microwave-assisted synthesis of nano-sized cadmium oxide as a new and highly efficient catalyst for solvent free acylation of amines and alcohols. Asian Journal of Chemistry. 2010;22(4):2554.
• 45. Majdalawieh A, Kanan MC, El-Kadri O, Kanan SM. Recent Advances in Gold and Silver Nanoparticles: Synthesis and Applications. Journal of Nanoscience and Nanotechnology. 2014 Jul 1;14(7):4757–80. Available from: <URL>.
• 46. Aldeen TS, Mohamed HEA, Maaza M. Bio-inspired Single Phase Monteponite CdO Nanoparticles via Natural Extract of Phoenix roebelenii Palm Leaves. Journal of Inorganic and Organometallic Polymers and Materials. 2020 Nov;30(11):4691–701. Available from: <URL>.
• 47. Kumar S, Ahmed B, Ojha AK, Das J, Kumar A. Facile synthesis of CdO nanorods and exploiting its properties towards supercapacitor electrode materials and low power UV irradiation driven photocatalysis against methylene blue dye. Materials Research Bulletin. 2017 Jun;90:224–31. Available from: <URL>.
• 48. Taiwade MA. Synthesis, Characterization of Nanocrystalline CdFe2O4, its Antibacterial Activity against Escherichia Coli. Der Pharma Chemica. 2013;5:301–6.