10.57647/j.ijc.2025.1501.07

Fe3O4@nano-coconut shell/Cu(II): A Unique and Reusable Catalyst for Green Synthesis of naphtho[1,3]oxazine Derivatives

  1. Department of Organic Chemistry, Faculty of Chemistry, College of Science, Yazd University, Yazd, Iran
Fe3O4@nano-coconut shell/Cu(II): A Unique and Reusable Catalyst for Green Synthesis of naphtho[1,3]oxazine Derivatives

Received: 2024-03-23

Revised: 2024-10-28

Accepted: 2025-01-08

Published 2025-01-08

How to Cite

Hajati, F., & Mirjalili, B. B. F. (2025). Fe3O4@nano-coconut shell/Cu(II): A Unique and Reusable Catalyst for Green Synthesis of naphtho[1,3]oxazine Derivatives. Iranian Journal of Catalysis, 15(1 (March 2025), 1-8. https://doi.org/10.57647/j.ijc.2025.1501.07

PDF views: 63

Abstract

Coconut shell nanoparticles were transformed into magnetic nanoparticles (Fe3O4@nano-coconut shell) that were utilized for Lewis acid (Cu(II)) support. Consequently, the synthesis of the Fe3O4@nano-coconut shell/Cu(II) catalyst, possessing easy and complete recovery capabilities, was achieved. The characterization of Fe3O4@nano-coconut shell/Cu(II) was conducted using various techniques, including FT-IR, FESEM, VSM, EDS-MAP, XRD, BET, and TGA. The catalytic efficacy of Fe3O4@nano-coconut shell/Cu(II) as a potent Lewis acid nano-catalyst was assessed for the manufacture of 2-aryl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine derivatives via a reaction of formaldehyde, aniline derivatives, and phenolic substrate such as β-naphthol. Fe3O4@nano-coconut shell/Cu(II) demonstrated robust performance in the reaction and could be reused up to four consecutive times with only a minor decline in catalytic activity.

Research Highlights

  • Fe3O4@nano-coconut shell/Cu(II) catalyst with a very easy and complete recovering ability was synthesized.
  • The synthesized catalyst was characterized by different techniques such as FT-IR, FESEM, VSM, EDS-MAP, XRD, BET as well as TGA.
  • The catalytic performance of Fe3O4@nano-coconut shell/Cu(II) was evaluated.
  • Synthesis of 2-aryl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine derivatives was done.
  • Fe3O4@nano-cocoanut shell/Cu(II) can be effective in reaction and reused four times.

Keywords

  • Fe3O4@nano-coconut shell/Cu (II),
  • Green Chemistry,
  • Magnetic nanoparticles,
  • Multi-component reactions,
  • 1,3-Oxazine

References

  1. T. Ahmadi, G.M. Ziarani, P. Gholamzadeh, H. Mollabagher, Tetrahedron: Asym. 28 (2017) 708-724. Doi: 10.1016/j.tetasy.2017.04.002
  2. C. Hulme, S. Chappeta, C. Griffith, Y.S. Lee, J. Dietrich, Tetrahedron Lett. 50 (2009) 1939-1942. Doi: 10.1016/j.tetlet.2009.02.099
  3. S. Verma, S.L. Jain, B. Sain, Tetrahedron Lett. 51 (2010) 6897-6900. Doi: 10.1016/j.tetlet.2010.10.124
  4. K. Tanaka, F. Toda, Chem. Rev. 100 (2000) 1025-1074. Doi: 10.1021/cr940089p
  5. Z.L. Shen, S.J. Ji, Synth. Commun. 39 (2009) 775-791. Doi: 10.1080/00397910802431149
  6. L. H. Reddy, J. L. Arias, J. Nicolas, P. Couvreur, Chem. Rev. 112 (2012) 5818-5878. Doi: 10.1021/cr300068p
  7. K. Zhou, X. Zhou, J. Liu, and Z. Huang, J. Pet. Sci. Eng. 188 (2020) 106943. Doi: 10.1016/j.petrol.2020.106943
  8. S. Zhang, H. Niu, Z. Hu, Y. Cai, Y. Shi, J. Chromatogr. A 1217 (2010) 4757-4764. Doi: 10.1016/j.chroma.2010.05.035
  9. K. Khoshnevisan, M. Barkhi, D. Zare, D. Davoodi, M. Tabatabaei, Synth. React. Inorg. Met-Org. Chem. 42 (2012) 644-648. Doi: 10.1080/15533174.2011.614997
  10. J. Safari, L. Javadian, RSC Adv. 4 (2014) 48973-48979. Doi: 10.1039/C4RA06618A
  11. V. A. J. Silva, P. L. Andrade, M. P. C. Silva, L.D.L.S. Valladares, J.A. Aguiar, J. Magn. Magn. Mater. 343 (2013) 138-143. Doi: 10.1016/j.jmmm.2013.04.062
  12. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111 (2011) 3036-3075. Doi: 10.1021/cr100230z
  13. R. B. Nasir Baig, R.S. Varma, Ind. Eng. Chem. Res. 53 (2014) 18625-18629. Doi: 10.1021/ie501081q
  14. S.A. Sadaphal, S.S. Sonar, B.B. Shingate, M.S. Shingare, Green. Chem. Lett. Rev. 3 (2010) 213-216. Doi: 10.1080/17518251003709522
  15. P.V. Shinde, A.H. Kategaonkar, B.B. Shingate, M.S. Shingare, Chin. Chem. Lett. 22 (2011) 915-918. Doi: 10.1016/J.CCLET.2011.01.011
  16. V.D. Dhakane, S.S. Gholap, U.P. Deshmukh, H.V. Chavan, B.P. Bandgar, C. R. Chim. 17 (2014) 431-436. Doi: 10.1016/j.crci.2013.06.002
  17. M. S. Al-Ajely, A. M. Noori, Bio med. J. Sci. Tech. Res. 29 (2020) 22510-22516. Doi: 10.26717/BJSTR.2020.29.004815
  18. S. S. Hosseinikhah, B. B. F. Mirjalili, N. Salehi, A. H. Bamoniri, RSC. Adv. 10 (2020) 40508-40513. Doi: 10.1039/D0RA07199D
  19. R. Borah, A.K. Dutta, P. Sarma, C. Dutta, B. Sarma, RSC Adv. 4 (2014) 10912-10917. Doi: 10.1039/C3RA47211F
  20. C.S. Higham, D.P. Dowling, J.L. Shaw, A. Cetin, C.J. Ziegler, J.R. Farrell, Tetrahedron lett. 47 (2006) 4419-4423. Doi: 10.1016/j.tetlet.2006.04.077
  21. W.J. Burke, E.M. Glennie, C. Weatherbee, Org. Chem. 29 (1964) 909-912. Doi: 10.1021/jo01027a038
  22. R.A. Sheldon, Green. Chem. 7 (2005) 267-278. Doi: 10.1039/B418069K
  23. M. Zhang, Q.Y. Fu, G. Gao, H.Y. He, Y. Zhang, Y.S. Wu, Z.H. Zhang, ACS Sustain. Chem. Eng. 7 (2017) 6175-6182. Doi: 10.1021/acssuschemeng.7b01102
  24. O.L. Keller Jr, Inorg. Chem. 2 (1963) 783-787. Doi: 10.1021/ic50008a029
  25. E. Babaei, B. F. Mirjalili, Polycycl. Aromat. Comp. 41 (2021) 518-525. Doi:10.1080/10406638.2019.1600561.
  26. S. S. Ganesan, N. Rajendran, S. I. Sundarakumar, A. Ganesan and B. Pemiah, Synthesis 45 (2013) 1564-1568. Doi: 10.1055/s-0033-1338430.
  27. M.V. Reddy, K.T. Lim, J.T. Kim, Y.T. Jeong, J. Chem. Res. 7 (2012) 398-401. Doi: 10.3184/174751912X1337166261377.
  28. A. D. Tafti, B. F. Mirjalili, RSC Adv. 10 (2020) 31874–31880. Doi: 10.1039/D0RA04282J
  29. Ganesan, S. S.; Rajendran, N.; Sundarakumar, S. I.; Ganesan, A.; Pemiah. B. Synthesis, 45 (2013) 1564-1568. Doi: 10.1055/s-0033-1338430
  30. V. D. Dhakane, S. S. Gholap, U. P. Deshmukh, H. V. Chavan, Bandgar. B. P. C. R. Chim. 17 (2014) 431-436. Doi: 10.1016/j.crci.2013.06.002
  31. S. Khabnadideh, A. solhjoo, R. Heidari, L Amiri Zirtol, A Sakhteman, Z. Rezaei, E. Babaei, S. Rahimi, L. Emami. BMC Chemistry. 16 (2022) 1-18. Doi: 10.1186/s13065-022-00836-8.
  32. M. Keihanfar, B. F. Mirjalili. Sci. Rep. 12 (2022) 17713-17724. Doi: 10.1038/s41598-022-22712-0.
  33. T. Lohar, A. Mane, S. Kamat, R. Salunkhe. Polycycl. Aromat. Comp. 40 (2020) 1210-1222. Doi: 10.1080/10406638.2018.1538057