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Preparation and characterization of novel hybrid nanomaterial catalyst MCM-41@AzaCrown-SB-Cu and its application in synthesis of 1, 2, 3-triazole derivatives in click chemistry

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Abstract

Synthesis of efficient and reusable catalyst was carried out by immobilization of azacrown ether onto the covalently linked amine-functionalized mesoporous MCM-41 via a simple method. Application of this linked azacrown ether functionalized MCM-41 catalyst was also investigated as an effective, heterogeneous and host material in the regioselective ring opening and triazole cyclization of epoxides by phenylacetylene and sodiumazide in click reaction. The heterogeneous catalyst was characterized by TGA,XRD,TEM, 1HNMR, 13CNMR and FT-IR techniques. The results of theses analysis showed that, MCM-41@azacrown-Cu with a 22.99% mol loading of copper has given excellent catalytic activity and high efficiency in short time. It is noted that one of the most valuable factors in this work is the recyclability of the catalyst.

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References

  1. T.V. Kovalchuk, H. Sfihi, A.S. Korchev, A.S. Kovalenko, V.G. Il'in, V.N. Zaitsev, J. Phys. Chem. B 109 (2005)

  2. V. Jarian, M. Vera, C. Pegie, Beilstein. J. Nanotechnol. 2, (2011) Doi:10.3762/bjnano.2.87

  3. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, J. Nat 359, 710–712 (1992)

    Article  CAS  Google Scholar 

  4. M. Kato, T. Shigeno, T. Kimura, K. Kuroda, Chem. Mater 17, 25 (2005). https://doi.org/10.1021/cm0505749

    Article  CAS  Google Scholar 

  5. D. Xueya, S. Hua, S. Hualin, G. Jing, L. Feng, L. Yanxiu, React. Kinet. Catal. Lett 44, 4 (2019). https://doi.org/10.1177/1468678319825909

    Article  CAS  Google Scholar 

  6. R. Narayan, U.Y. Nayak, A.M. Raichur, S. Garg, Advances. Pharmaceutics 10, 3 (2018). https://doi.org/10.3390/pharmaceutics10030118

    Article  CAS  Google Scholar 

  7. H. Sharghi, R. Khalifeh, A. R. Salimi Beni, I. R .J. Iran. Chem. Soc 7, 275–288 (2010).

  8. K. Maeda, N. Shinyashiki, S. Yagihara, S. Wiegand, R. Kita, J. Chem. Phys 143, 124504 (2015). https://doi.org/10.1063/1.4931115

    Article  CAS  PubMed  Google Scholar 

  9. S. Barmana, M. Nath Roy, RSC. Adv 6, 76381–76389 (2016). Doi:10.1039/C6RA14138B

  10. G. Chehardoli, A. Bahmani, Supramol. Chem. 31(4), 221 (2019). https://doi.org/10.1080/10610278.2019.1568432

    Article  CAS  Google Scholar 

  11. C. Yoo, H. M. Dodgea, A. J. M. Miller, Chem. Comm 00 (2019). Doi:10.1039/C9CC00803A

  12. T. Kojima, F. Ogishima, T. Nishibu, H. Kotani, T. Ishizuka, T. Okajima, S. Nozawa, Y. Shiota, K. Yoshizawa, H. Ohtsu, M. Kawano, T. Shiga, H. Oshio, Inorg. Chem 57, 9683–9695 (2018). https://doi.org/10.1021/acs.inorgchem.8b00037

    Article  CAS  PubMed  Google Scholar 

  13. A. Viso, R. Fernández de la Pradilla, A. García, A. Flores, Chem. Rev 105 (2005). Doi:10.1021/cr0406561

  14. S. H. Sumrra, M. Ibrahim, S. Ambreen, M. Imran, M. Danish, F. Sultana Rehmani, Bioinorg. Chem. Appl (2014). Doi:10.1155/2014/812924

  15. M. Whiting, J. Muldoon, Y.C. Lin, S.M. Silverman, W. Lindstrom, A.J. Olson, H.C. Kolb, M.G. Finn, K.B. Sharpless, Elder JH, Fokin VV. Angew. Chem. Int. Ed 45, 9 (2006). https://doi.org/10.1002/anie.200502161

    Article  CAS  Google Scholar 

  16. Y. Bourne, H.C. Kolb, Z. Radić, K.B. Sharpless, P. Taylor, P. Marchot, Natl. Acad. Sci. USA 101, 6 (2004). https://doi.org/10.1073/pnas.0308206100

    Article  CAS  Google Scholar 

  17. J. Thomas, J. John, N. Parekh, W. Dehaen, Angew. Chem. Int. Ed. Engl 53, 38 (2014). https://doi.org/10.1002/anie.201403453

    Article  CAS  Google Scholar 

  18. T. W. Kim, Y. Yong, S. Y. Shin, H. Jung, K. H. Park, Y. H. Lee, Y. Lim, K. Y. Jung. Bioorg. Chem 59 (2015). Doi:10.1016/j.bioorg

  19. A. Faruk, K.D. Biplob, J. Pharm. Chem. Biol. Sci 2(4), 235–247 (2014)

    Google Scholar 

  20. W. G. Lewis, L. G. Green, F. Grynszpan, Z. Radic, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless, Angew. Chem 114 (2002). Doi:10.1002/1521–3757(20020315)114:6

  21. N. Akira, K. Hisashi, S. Taketoshi, S. Hirosada, K. Morio, S. Yasushi. J. Med. Chem 20 (1977). Doi:10.1021/jm00211a030

  22. G. Ye, T. Lan, Z.X. Huang, X.N. Cheng, C.Y. Cai, S.M. Ding, M.L. Xie, Eur. J. Med. Chem 1, 362–373 (2019). https://doi.org/10.1016/j.ejmech.2019.05.045

    Article  CAS  Google Scholar 

  23. T. El Malah, H. F. Nour, A. Satti, B. A. Hemdan, W. A. El-Sayed Molecules 25, 4 790 (2020). Doi:10.3390/molecules25040790

  24. A. R. Modarresi Alam, M. Nasrollahzadeh, Tetrahedron. Lett 33 (2009). Doi:10.3906/kim-0808–44

  25. V. A. Ostrovskii, R. E. Trifonov, E. A. Popova, Russ. Chem. Bull 61 (2012).

  26. C. Menendez, A. Chollet, F. Rodriguez, C. Inard, M. R. Pasca, C. Lherbet, M. Baltas, Eur. J. Med. Chem 52 (2012). Doi:10.1016/j.ejmech

  27. E.S. Hadi, E. Hossien, L. Jalil, R. Amin, Appl. Organomet. Chem 32, 1 (2017). https://doi.org/10.1002/aoc.3947

    Article  CAS  Google Scholar 

  28. V. A. Blanca Ivonne, L. R. Leticia, A. B. Deyanira, N. S. Guillermo Enrique, G. C. Atilano, H. L. Víctor, M. S. José Antonio, J. Tetrahedron. Lett 58 (2017). Doi:10.1016/j.tetlet.2017.05.055

  29. J. L. Li, Y. Q. Zhang, Y. Zhang, A. L. Zhu, J. S. Zhang, Chinese. Chemical. Letters 25 (2010). Doi:10.1016/j.cclet.2014.03.004

  30. M.C. Giel, C.J. Smedley, E.R.R. Mackie, T. Guo, J. Dong, T.P.S. da Costa, J. E. Moses Chem. Rxiv 211, 2464 (2019). https://doi.org/10.26434/chemrxiv.9937754.v1

    Article  Google Scholar 

  31. D.H. Christopher, L. Xin-Ming, W. Dong, Pharm. Res 25, 10 (2008). https://doi.org/10.1007/s11095-008-9616-1

    Article  CAS  Google Scholar 

  32. V. R. Vsevolod, G. G. Luke, V. F. Valery, S. K Barry, Angew. Chem 41 (2002). Doi:10.1002/1521–3773(20020715)41

  33. A. Heather, D.R. Rosemary, W.M. Steven, N. Arundhati, Y. Woon-Seok, E.H. Jason, M.P. Suresh, A.T. Abdul, M.B. Vanessa, J.K. Russell, V.F. Valery, S. Barry, R.H. James, Angew Chem Int Ed Engl 48, 27 (2009). https://doi.org/10.1002/anie.200900488

    Article  CAS  Google Scholar 

  34. D.B. Jovica, B. Vincenzo, C. Alberto, N.L. James, S. Serena, S. Fraser, Chem. Eur. J 10, 8 (2002). https://doi.org/10.1002/chem.200305687

    Article  CAS  Google Scholar 

  35. S. Díez González, A. Correa, L. Cavallo, S. P. Nolan, Chem. Eur .J 12 (2006).

  36. O.S. Miljanić, W.R. Dichtel, S.I. Khan, S. Mortezaei, J.R. Heath, J.F. Stoddart, J. Am. Chem. Soc 129, 26 (2007)

    Article  Google Scholar 

  37. F. Grégory, K. Ashok, Chem. Commun 0 (2008). Doi:10.1039/B809870K

  38. S. Li, L. Wang, F. Yu, Z. Zhu, D. Shobaki, H. Chen, M. Wang, J. Wang, G. Qin, U.J. Erasquin, L. Ren, Y. Wangb, C. Cai, Chem. Soi 8(3), 2107–2114 (2017)

    CAS  Google Scholar 

  39. W.R. Dichtel, O.S. Miljanić, J.M. Spruell, J.R. Heath, J.F. Stoddart, J. Am. Chem. Soc 128, 32 (2006). https://doi.org/10.1021/ja063127i

    Article  CAS  Google Scholar 

  40. M. Michael, S. Kristin, D. Eric, J.H. Craig, P.R. Thomas, W. Peng, V.F. Valery, Macromolecules 38(9), 3663 (2005). https://doi.org/10.1021/ma047657f

    Article  CAS  Google Scholar 

  41. L. Yu Heng, J. R. Peter, W. Michael, H. T. Matthew, Chem. Soc. Rev 40 (2011). Doi:10.1039/C0CS00143K

  42. G. A. Burley, J. Gierlich, M. R. Mofid, H. Nir, S. Tal, Y. Eichen, T. Carell, J. Am. Chem. Soc 128 (2006). Doi:10.1021/ja055517v

  43. T. Ishizuka, H.S. Liu, K. Ito, Y. Xu, Sci. Rep 6, 33217 (2016). https://doi.org/10.1038/srep33217

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. R. Mohammad Reza, G. Shahriar, T. Mahbobeh, S. Sajjad J Med Chem 13, 1 (2013). Doi:10.5829/idos

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Acknowledgements

We gratefully acknowledge the support of this work by Yasouj University Research Council.

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  1. Department of Chemistry, Yasouj University, Yasouj, Iran

    Somayeh shirali & Alireza Salimi Beni

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  1. Somayeh shirali
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Correspondence to Alireza Salimi Beni.

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shirali, S., Beni, A.S. Preparation and characterization of novel hybrid nanomaterial catalyst MCM-41@AzaCrown-SB-Cu and its application in synthesis of 1, 2, 3-triazole derivatives in click chemistry. J Porous Mater 27, 1601–1611 (2020). https://doi.org/10.1007/s10934-020-00924-x

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