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A novel magnetically recyclable silver-loaded cellulose-based bionanocomposite catalyst for green synthesis of tetrazolo[1,5-a]pyrimidines

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Abstract

5-Methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic ester derivatives were efficiently synthesized by reaction of methyl or ethyl acetoacetate, 5-aminotetrazole (produced from 2-cyanoguanidine and sodium azide), and various aromatic aldehydes in presence of a new cellulose-based Ag-loaded magnetic bionanostructure. This protocol offers many advantages such as short reaction time, high yield, the remarkable magnetic property of the nanocomposite, and easy separation of the nanocatalyst from the reaction mixture without considerable loss of catalytic activity. Furthermore, X-ray diffraction analysis, field-emission scanning electron microscopy, and energy-dispersive X-ray (EDX) analysis were used to characterize the prepared nanocatalyst.

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References

  1. F. Bauer, U. Decker, H. Ernst, M. Findeisen, H. Langguth, R. Mehnert, V. Sauerland, R. Hinterwaldner, Int. J. Adhes. 26, 567–570 (2006)

    Article  CAS  Google Scholar 

  2. P. Innocenzi, B. Lebeau, J. Mater. Chem. 15, 3821–3831 (2005)

    Article  CAS  Google Scholar 

  3. M. Darder, E. Ruiz-Hitzky, J. Mater. Chem. 15, 3913–3918 (2005)

    Article  CAS  Google Scholar 

  4. C. Sanchez, B. Julián, P. Belleville, M. Popall, J. Mater. Chem. 15, 3559–3592 (2005)

    Article  CAS  Google Scholar 

  5. Y. Feng, J. Zhang, J. He, J. Zhang, Carbohydr. Polym. 147, 171–177 (2016)

    Article  CAS  Google Scholar 

  6. K. Kueseng, K.I. Jacob, Eur. Polym. J. 42, 220–227 (2006)

    Article  CAS  Google Scholar 

  7. V.L. Finkenstadt, Appl. Microbiol. Biotechnol. 67, 735–745 (2005)

    Article  CAS  Google Scholar 

  8. D. Klemm, B. Heublein, H. Fink, A. Bohn, Angew. Chem. Int. Ed. 44, 3358–3393 (2005)

    Article  CAS  Google Scholar 

  9. W. Zhu, W. Li, Y. He, T. Duan, Appl. Surf. Sci. 338, 22–26 (2015)

    Article  CAS  Google Scholar 

  10. H. Ullah, F. Wahid, H.A. Santos, T. Khan, Carbohydr. Polym. 150, 330–352 (2016)

    Article  CAS  Google Scholar 

  11. S.-M. Li, N. Jia, M.-G. Ma, Z. Zhang, Q.-H. Liu, R.-C. Sun, Carbohydr. Polym. 86, 441–447 (2011)

    Article  CAS  Google Scholar 

  12. R.T. Olsson, M.A.S.A. Samir, G. Salazar-Alvarez, L. Belova, V. Ström, L.A. Berglund, O. Ikkala, J. Nogues, U.W. Gedde, Nat. Nanotechnol. 5, 584–588 (2010)

    Article  CAS  Google Scholar 

  13. S.J. Eichhorn, A. Dufresne, M. Aranguren, N.E. Marcovich, J.R. Capadona, S.J. Rowan, C. Weder, W. Thielemans, M. Roman, S. Renneckar, J. Mater. Sci. 45, 1–33 (2010)

    Article  CAS  Google Scholar 

  14. S.-M. Li, N. Jia, J.-F. Zhu, M.-G. Ma, F. Xu, B. Wang, R.-C. Sun, Carbohydr. Polym. 83, 422–429 (2011)

    Article  CAS  Google Scholar 

  15. Y.-Y. Dong, S.-M. Li, M.-G. Ma, K. Yao, R.C. Sun, Carbohydr. Polym. 106, 14–21 (2014)

    Article  CAS  Google Scholar 

  16. F. Quignard, A. Choplin, Chem. Commun. 1, 21–22 (2001)

    Article  Google Scholar 

  17. E. Coronado, C. Martí-Gastaldo, E. Navarro-Moratalla, A. Ribera, S.J. Blundell, P.J. Baker, Nat. Chem. 2, 1031–1036 (2010)

    Article  CAS  Google Scholar 

  18. S. Lin, Y. Cheng, J. Liu, M.R. Wiesner, Langmuir 28, 4178–4186 (2012)

    Article  CAS  Google Scholar 

  19. U. Chatterjee, S.K. Jewrajka, S. Guha, Polym. Compos. 30, 827–834 (2009)

    Article  CAS  Google Scholar 

  20. A. Maleki, H. Movahed, R. Paydar, RSC Adv. 6, 13657–13665 (2016)

    Article  CAS  Google Scholar 

  21. A. Maleki, A. Sarvary, RSC Adv. 5, 60938–60955 (2015)

    Article  CAS  Google Scholar 

  22. A. Sarvary, A. Maleki, Mol. Divers. 19, 189–212 (2015)

    Article  CAS  Google Scholar 

  23. O.V. Fedorova, M.S. Zhidovinova, G.L. Rusinov, I.G. Ovchinnikova, Russ. Chem. Bull. 52, 1768–1769 (2003)

    Article  CAS  Google Scholar 

  24. J. Hashim, N. Arshad, I. Khan, S. Nisar, B. Ali, M.I. Choudhary, Tetrahedron 70, 8582–8587 (2014)

    Article  CAS  Google Scholar 

  25. P.N. Gaponik, S.V. Voitekhovich, O.A. Ivashkevich, Russ. Chem. Rev. 75, 507–539 (2006)

    Article  CAS  Google Scholar 

  26. V.A. Chebanov, Y.I. Sakhno, S.M. Desenko, S.V. Shishkina, V.I. Musatov, O.V. Shishkin, I.V. Knyazeva, Synthesis 2005, 2597–2601 (2005)

    Article  Google Scholar 

  27. J. Zhu, H. Bienaymé, Multicomponent reactions (Wiley, Hoboken, 2006)

    Google Scholar 

  28. L. Weber, Curr. Med. Chem. 9, 2085–2093 (2002)

    Article  CAS  Google Scholar 

  29. A. Maleki, H. Movahed, P. Ravaghi, Carbohydr. Polym. 156, 259–267 (2017)

    Article  CAS  Google Scholar 

  30. A. Maleki, H. Movahed, P. Ravaghi, T. Kari, RSC Adv. 6, 98777–98787 (2016)

    Article  CAS  Google Scholar 

  31. A. Maleki, M. Aghaei, H.R. Hafizi-Atabak, M. Ferdowsi, Ultrason. Sonochem. 37, 260–266 (2017)

    Article  CAS  Google Scholar 

  32. A. Maleki, M. Aghaei, R. Paydar, J. Iran. Chem. Soc. 14, 485–490 (2017)

    Article  CAS  Google Scholar 

  33. A. Maleki, T. Kari, M. Aghaei, J. Porous Mater. doi: 10.1007/s10934-017-0388-z

  34. C. Yao, S. Lei, C. Wang, C. Yu, S. Tu, J. Heterocycl. Chem. 45, 1609–1613 (2008)

    Article  CAS  Google Scholar 

  35. V.L. Gein, I.N. Vladimirov, O.V. Fedorova, A.A. Kurbatova, N.V. Nosova, I.V. Krylova, M.I. Vakhrin, Russ. J. Org. Chem. 46, 699–705 (2010)

    Article  CAS  Google Scholar 

  36. A. Haleel, P. Arthi, N.D. Reddy, V. Veena, N. Sakthivel, Y. Arun, P.T. Perumal, A.K. Rahiman, RSC Adv. 4, 60816–60830 (2014)

    Article  CAS  Google Scholar 

  37. A. Haleel, D. Mahendiran, V. Veena, N. Sakthivel, A.K. Rahiman, Mater. Sci. Eng. C 68, 366–382 (2016)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge partial support from the Research Council of the Iran University of Science and Technology.

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Authors and Affiliations

  1. Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran

    Ali Maleki, Parisa Ravaghi, Morteza Aghaei & Hamed Movahed

Authors
  1. Ali Maleki
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  2. Parisa Ravaghi
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  3. Morteza Aghaei
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  4. Hamed Movahed
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Correspondence to Ali Maleki.

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Maleki, A., Ravaghi, P., Aghaei, M. et al. A novel magnetically recyclable silver-loaded cellulose-based bionanocomposite catalyst for green synthesis of tetrazolo[1,5-a]pyrimidines. Res Chem Intermed 43, 5485–5494 (2017). https://doi.org/10.1007/s11164-017-2941-4

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  • DOI: https://doi.org/10.1007/s11164-017-2941-4

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