Abstract
Nano-magnetite-supported sulfated polyethylene glycol (Fe3O4@PEG-SO3H) was prepared, characterized and utilized as a magnetically recoverable heterogeneous catalyst for the one-pot, three-component reaction of 2-aminobenzothiazole, aldehydes and 2-naphthol/isatoic anhydride resulting in efficient formation of 1-(benzothiazolylamino)arylmethyl-2-naphthol or dihydroquinazolinones derivatives. The significant features of this method include green conditions, operational simplicity, minimizing production of chemical waste, shorter reaction times and good to high yields. In addition, the nanocatalyst can easily be separated from the reaction mixture by application of a magnetic field and reused without significant deterioration in its catalytic activity.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Zamani Kouhpanji, M. R., Stadler, B. J. Sensors 2020, 20, 2554 (37 pages). https://doi.org/10.3390/s20092554.Search in Google Scholar
2. Amiri, M., Salavati-Niasari, M., Akbari, A. Adv. Colloid Interface Sci. 2019, 265, 29–44. https://doi.org/10.1016/j.cis.2019.01.003.Search in Google Scholar
3. Zhou, K., Zhou, X., Liu, J., Huang, Z. J. Pet. Sci. Eng. 2020, 188, 106943. https://doi.org/10.1016/j.petrol.2020.106943.Search in Google Scholar
4. Xiao, D., Lu, T., Zeng, R., Bi, Y. Microchim. Acta 2016, 183, 2655–2675. https://doi.org/10.1007/s00604-016-1928-y.Search in Google Scholar
5. Khatami, M., Alijani, H. Q., Nejad, M. S., Varma, R. S. Appl. Sci. 2018, 8, 411. https://doi.org/10.3390/app8030411.Search in Google Scholar
6. Gawande, M. B., Goswami, A., Asefa, T., Guo, H., Biradar, A. V., Peng, D. L., Zboril, R., Varma, R. S. Chem. Soc. Rev. 2015, 44, 7540–7590. https://doi.org/10.1039/c5cs00343a.Search in Google Scholar
7. Chaudhuri, R. G., Paria, S. Chem. Rev. 2012, 112, 2373–2433.10.1021/cr100449nSearch in Google Scholar PubMed
8. Kothandapani, J., Ganesan, S. S. Curr. Org. Chem. 2019, 23, 313–334. https://doi.org/10.2174/1385272823666190312152209.Search in Google Scholar
9. Hassani, H., Nasseri, M. A., Zakerinasab, B., Rafiee, F. Appl. Organomet. Chem. 2016, 30, 408–413. https://doi.org/10.1002/aoc.3447.Search in Google Scholar
10. Maleki, A., Zand, P., Mohseni, Z. RSC Adv. 2016, 6, 110928–110934. https://doi.org/10.1039/c6ra24029a.Search in Google Scholar
11. Safaei-Ghomi, J., Shahbazi-Alavi, H., Babaei, P. Z. Naturforsch. 2016, 71b, 849–856. https://doi.org/10.1515/znb-2016-0041.Search in Google Scholar
12. Kamali, F., Shirini, F. Appl. Organomet. Chem. 2018, 32, e3972 (12 pages). https://doi.org/10.1002/aoc.3972.Search in Google Scholar
13. Abarghooei, M. A., Mohebat, R., Karimi-Jaberi, Z., Mosslemin, M. H. J. Chem. Res. 2017, 41, 408–412. https://doi.org/10.3184/174751917x14967701767012.Search in Google Scholar
14. Bonyasi, F., Hekmati, M., Veisi, H. J. Colloid Interface Sci. 2017, 496, 177–187. https://doi.org/10.1016/j.jcis.2017.02.023.Search in Google Scholar
15. Maleki, A., Firouzi-Haji, R. Inorg Nano-Met. Chem. 2019, 49, 132–135. https://doi.org/10.1080/24701556.2019.1577258.Search in Google Scholar
16. Ashraf, M. A., Liu, Z., Peng, W. X., Zhou, L. Catal. Lett. 2020, 150, 1128–1141. https://doi.org/10.1007/s10562-019-02973-7.Search in Google Scholar
17. Bondock, S., Fadaly, W., Metwally, M. A. J. Sulfur Chem. 2009, 30, 74–107. https://doi.org/10.1080/17415990802588033.Search in Google Scholar
18. Hutchinson, I., Chua, M. S., Browne, H. L., Trapani, V., Bradshaw, T. D., Westwell, A. D., Stevens, M. F. G. J. Med. Chem. 2001, 44, 1446–1455. https://doi.org/10.1021/jm001104n.Search in Google Scholar
19. Keri, R. S., Patil, M. R., Patil, S. A., Budagumpi, S. Eur. J. Med. Chem. 2015, 89, 207–251. https://doi.org/10.1016/j.ejmech.2014.10.059.Search in Google Scholar
20. Gjorgjieva, M., Tomašič, T., Kikelj, D. L., Masic, P. Curr. Med. Chem. 2018, 25, 5218–5236.10.2174/0929867324666171009103327Search in Google Scholar PubMed
21. Payaz, D. U., Küçükbay, F. Z., Küçükbay, H., Angeli, A., Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2019, 34, 343–349. https://doi.org/10.1080/14756366.2018.1553040.Search in Google Scholar
22. Hopper, R. J. Rubber Chem. Technol. 1993, 66, 623–633. https://doi.org/10.5254/1.3538334.Search in Google Scholar
23. Zhang, X. H., Wong, O. Y., Gao, Z. Q., Lee, C. S., Kwong, H. L., Wu, S. K. Mater. Sci. Eng. B 2001, 85, 182–185. https://doi.org/10.1016/s0921-5107(01)00607-9.Search in Google Scholar
24. Prajapati, N. P., Vekariya, R. H., Borad, M. A., Patel, H. D. RSC Adv. 2014, 4, 60176–60208. https://doi.org/10.1039/c4ra07437h.Search in Google Scholar
25. Dadmal, T. L., Katre, S. D., Mandewale, M. C., Kumbhare, R. M. New J. Chem. 2018, 42, 776–797. https://doi.org/10.1039/c7nj03776g.Search in Google Scholar
26. Cardellicchio, C., Capozzi, M. A., Naso, F. Tetrahedron: Asymmetry 2010, 21, 507–517. https://doi.org/10.1016/j.tetasy.2010.03.020.Search in Google Scholar
27. Adrom, B., Maghsoodlou, M. T., Hazeri, N., Lashkari, M. Res. Chem. Intermed. 2015, 41, 7553–7560. https://doi.org/10.1007/s11164-014-1843-y.Search in Google Scholar
28. Javanshir, S., Ohanian, A., Heravi, M. M., Naimi-Jamal, M. R., Bamoharram, F. F. J. Saudi Chem. Soc. 2014, 18, 502–506. https://doi.org/10.1016/j.jscs.2011.10.013.Search in Google Scholar
29. Maghsoodlou, M. T., Karima, M., Lashkari, M., Adrom, B., Aboonajmi, J. J. Iran. Chem. Soc. 2017, 14, 329–335. https://doi.org/10.1007/s13738-016-0981-0.Search in Google Scholar
30. Shaterian, H. R., Hosseinian, A. Res. Chem. Intermed. 2015, 41, 793–801. https://doi.org/10.1007/s11164-013-1230-0.Search in Google Scholar
31. Seddighi, M., Shirini, F., Mamaghani, M. Comp. Rend. Chim. 2015, 18, 573–580. https://doi.org/10.1016/j.crci.2014.09.003.Search in Google Scholar
32. Lati, M. P., Shirini, F., Alinia-Asli, M., Rezvani, M. A. J. Iran. Chem. Soc. 2018, 15, 1655–1662. https://doi.org/10.1007/s13738-018-1364-5.Search in Google Scholar
33. Damghani, F. K., Pourmousavi, S. A., Kiyani, H. Curr. Org. Synth. 2019, 16, 1040–1054. https://doi.org/10.2174/1570179416666190725101422.Search in Google Scholar
34. Torabi, M., Yarie, M., Zolfigol, M. A., Azizian, S. Res. Chem. Intermed. 2020, 46, 891–907. https://doi.org/10.1007/s11164-019-03996-w.Search in Google Scholar
35. Badolato, M., Aiello, F., Neamati, N. RSC Adv. 2018, 8, 20894–20921. https://doi.org/10.1039/c8ra02827c.Search in Google Scholar
36. Khan, I., Ibrar, A., Abbas, N., Saeed, A. Eur. J. Med. Chem. 2014, 76, 193–244. https://doi.org/10.1016/j.ejmech.2014.02.005.Search in Google Scholar
37. Hameed, A., Al-Rashida, M., Uroos, M., Ali, S. A., Ishtiaq, M., Khan, K. M. Expert Opin. Ther. Pat. 2018, 28, 281–297. https://doi.org/10.1080/13543776.2018.1432596.Search in Google Scholar
38. Shaabani, A., Rahmati, A., Moghimi, R. Comp. Rend. Chim. 2008, 11, 759–764. https://doi.org/10.1016/j.crci.2007.11.007.Search in Google Scholar
39. Shaterian, H. R., Oveisi, A. R., Honarmand, M. Synth. Commun. 2010, 40, 1231–1242. https://doi.org/10.1080/00397910903064831.Search in Google Scholar
40. Anizadeh, M. R., Zolfigol, M. A., Yarie, M., Torabi, M., Azizian, S. Res. Chem. Intermed. 2020, 46, 3945–3960. https://doi.org/10.1007/s11164-020-04183-y.Search in Google Scholar
41. Khurana, J. M., Kumar, S. Green Chem. Lett. Rev. 2011, 4, 321–325. https://doi.org/10.1080/17518253.2011.571718.Search in Google Scholar
42. Ziarani, G. M., Seiedakbari, L., Gholamzadeh, P., Badiei, A. Iran. J. Catal. 2017, 7, 137–145.Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2021-0010).
© 2021 Walter de Gruyter GmbH, Berlin/Boston
