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Preparation and characterization of a novel organic–inorganic hybrid nanostructure: application in synthesis of spirocompounds

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Abstract

Immobilization and heterogenization of acidic/basic groups or organic tags on inorganic supports have found many important applications in recent years. In this investigation, a new hybrid organic–inorganic nanostructure was prepared. The structure of novel nanomaterial was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis, vibrating sample magnetometer, scanning electron microscopy and the energy-dispersive X-ray spectroscopy techniques. The spirocompounds, especially spiroperimidines and pyranopyrazoles, are important structures with diverse biological activities and many applications in industries. So, the prepared hybrid nanomaterial was used as an efficient catalyst in the one-pot, green and simple protocol for the synthesis of pyranopyrazole, spiropyranopyrazole and spiroperimidine derivatives. The structure of some compounds is characterized by FT-IR, 1H-NMR and 13C-NMR analyses. In addition, the proposed intermediates were synthesized and identified to prove the presented mechanism of the reaction. This hybrid nanomaterial is a recyclable and highly efficient heterogeneous catalyst and easily separated by an external magnet from the reaction media. The short reaction time, high efficiency, operational safety and use of environmentally benign solvent are some benefits of this procedure.

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References

  1. K. Li, Y. Fan, Y. He, L. Zeng, X. Han, Y. Yan, Sci. Rep. 7, 1 (2017)

    Article  CAS  Google Scholar 

  2. A.A. Alqadami, M. Naushad, Z.A. Alothman, A.A. Ghfar, Appl. Mater. 9, 36026 (2017)

    CAS  Google Scholar 

  3. A.A. Alqadami, M. Naushad, M.A. Abdalla, T. Ahamad, Z.A. Alothman, S.M. Alshehri, A.A. Ghfar, J. Clean. Prod. 156, 426 (2017)

    Article  CAS  Google Scholar 

  4. Z. Rashid, H. Naeimi, A.-H. Zarnani, M. Nazari, M.-R. Nejadmoghaddam, R. Ghahremanzadeh, RSC Adv. 6, 36840 (2016)

    Article  CAS  Google Scholar 

  5. D. Wang, D. Astruc, Chem. Rev. 114, 6949 (2014)

    Article  CAS  PubMed  Google Scholar 

  6. M.A. Bodaghifard, M. Hamidinasab, N. Ahadi, Curr. Org. Chem. 22, 234 (2018)

    Article  CAS  Google Scholar 

  7. H. Tombuloglu, G. Tombuloglu, Y. Slimani, I. Ercan, H. Sozeri, A. Baykal, Environ. Pollut. 243, 872 (2018)

    Article  CAS  PubMed  Google Scholar 

  8. T. Kang, F. Li, S. Baik, W. Shao, D. Ling, T. Hyeon, Biomaterials 136, 98 (2017)

    Article  CAS  PubMed  Google Scholar 

  9. M. Jacintha, P. Neeraja, M. Sivakumar, K. Chinnaraj, J. Supercond. Novel. Magn. 30, 237 (2017)

    Article  CAS  Google Scholar 

  10. F. Bonyasi, M. Hekmati, H. Veisi, J. Colloid, Interface Sci. 496, 177 (2017)

    Article  CAS  Google Scholar 

  11. A.K. Rathi, R. Zboril, R.S. Varma, M.B. Gawande, Ferrites and Ferrates: Chemistry and Applications in Sustainable Energy and Environmental Remediation (ACS Publications, Washington, 2016), pp. 39–78

    Book  Google Scholar 

  12. F. Chen, J. Zheng, M. Huang, Y. Li, Res. Chem. Intermed. 41, 5545 (2015)

    Article  CAS  Google Scholar 

  13. H. Sachdeva, S. Khaturia, MOJ. Biorg. Org. Chem. 1, 239 (2017)

    Google Scholar 

  14. P.N. Sudhan, M. Ghashang, S.S. Mansoor, Beni Seuf. Univ. J. Appl. ScI. 5, 340 (2016)

    Google Scholar 

  15. F. Behbahani, F.M. Golchin, J. Taibah. Univ. Sci. 11, 85 (2017)

    Article  Google Scholar 

  16. R. Kumar, N. Yadav, R. Lavilla, D. Blasi, J. Quintana, J.M. Brea, M.I. Loza, J. Mestres, M. Bhandari, R. Arora, Mol. Divers. 21, 533 (2017)

    Article  CAS  PubMed  Google Scholar 

  17. A. Moshtaghi Zonouz, D. Moghani, Synth. Commun. 46, 220 (2016)

    Article  CAS  Google Scholar 

  18. V.V. Patil, G.S. Shankarling, Catal. Commun. 57, 138 (2014)

    Article  CAS  Google Scholar 

  19. N.A. Harry, R.M. Cherian, S. Radhika, G. Anilkumar, Tetrahedron Lett. 60, 150946 (2019)

    Article  CAS  Google Scholar 

  20. B.B.F. Mirjalili, M. Imani, J. Chin. Chem. Soc Taip. 66, 1542 (2019)

    Article  CAS  Google Scholar 

  21. Q. Niu, J. Xi, L. Li, L. Li, C. Pan, M. Lan, L. Rong, Tetrahedron Lett. 60, 151181 (2019)

    Article  CAS  Google Scholar 

  22. Z. Wang, L. Gao, Z. Xu, Z. Ling, Y. Qin, L. Rong, S.-J. Tu, Tetrahedron 73, 385 (2017)

    Article  CAS  Google Scholar 

  23. H. Naeimi, S. Lahouti, RSC Adv. 7, 2555 (2017)

    Article  CAS  Google Scholar 

  24. B. Maleki, N. Nasiri, R. Tayebee, A. Khojastehnezhad, H.A. Akhlaghi, RSC Adv. 6, 79128 (2016)

    Article  CAS  Google Scholar 

  25. G.M. Ziarani, M. Rahimifard, F. Nouri, A. Badiei, J. Serb. Chem. Soc. 80, 1265 (2015)

    Article  CAS  Google Scholar 

  26. M. Abdi, S. Rostamizadeh, N. Zekri, Polycycl. Aromat. Compd. 39, 413 (2019)

    Article  CAS  Google Scholar 

  27. M.A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. Soc. 14, 365 (2017)

    Article  CAS  Google Scholar 

  28. H. Kefayati, S.J. Bazargard, P. Vejdansefat, S. Shariati, A.M. Kohankar, Dyes Pigm. 125, 309 (2016)

    Article  CAS  Google Scholar 

  29. A. Javid, A. Khojastehnezhad, H. Eshghi, F. Moeinpour, F.F. Bamoharram, J. Ebrahimi, Org. Prep. Proced. Int. 48, 377 (2016)

    Article  CAS  Google Scholar 

  30. N. Ahadi, M.A. Bodaghifard, A. Mobinikhaledi, Appl. Organomet. Chem. 33, e4738 (2019)

    Article  CAS  Google Scholar 

  31. J.-Q. Zhu, X.-J. Zhang, S.-W. Wang, G.-S. Wang, P.-G. Yin, RSC Adv. 6, 88104 (2016)

    Article  CAS  Google Scholar 

  32. J. Li, H. Zhao, X. Hou, W. Fa, J. Cai, Micro. Nano Lett. 12, 53 (2017)

    Article  CAS  Google Scholar 

  33. M.A. Bodaghifard, N. Ahadi, Iran. J. Catal. 6, 377 (2016)

    CAS  Google Scholar 

  34. V.D. Patil, K.P. Patil, N.R. Sutar, P.V. Gidh, Chem. Int. 3, 195 (2017)

    CAS  Google Scholar 

  35. A.R. Moosavi-Zare, M.A. Zolfigol, R. Salehi-Moratab, E. Noroozizadeh, J. Mol. Catal. A. Chem. 415, 144 (2016)

    Article  CAS  Google Scholar 

  36. R.-Y. Guo, Z.-M. An, L.-P. Mo, S.-T. Yang, H.-X. Liu, S.-X. Wang, Z.-H. Zhang, Tetrahedron 69, 9931 (2013)

    Article  CAS  Google Scholar 

  37. K.G. Patel, N.M. Misra, R.H. Vekariya, R.R. Shettigar, Res. Chem. Intermed. 44, 289 (2018)

    Article  CAS  Google Scholar 

  38. A.S. Waghmare, S.S. Pandit, D.M. Suryawanshi, Comb. Chem. High. Throughput Screen. 21, 254 (2018)

    Article  CAS  PubMed  Google Scholar 

  39. M. Fatahpour, F.N. Sadeh, N. Hazeri, M.T. Maghsoodlou, M. Lashkari, J. Iran. Chem. Soc. 14, 1945 (2017)

    Article  CAS  Google Scholar 

  40. T. Liu, C.B. Li, Y.Q. Yu, D.Z. Xu, ChemistrySelect 2, 2917 (2017)

    Article  CAS  Google Scholar 

  41. S.F. Hojati, A. Amiri, S. Mohamadi, N. MoeiniEghbali, Res. Chem. Intermed. 44, 2275 (2018)

    Article  CAS  Google Scholar 

  42. P. Farokhian, M. Mamaghani, N.O. Mahmoodi, K. Tabatabaeian, J. Iran. Chem. Soc. 15, 11 (2018)

    Article  CAS  Google Scholar 

  43. A.R. Moosavi-Zare, H. Goudarziafshar, K. Saki, Appl. Organomet. Chem. 32, e3968 (2018)

    Article  CAS  Google Scholar 

  44. Y.A. Tayade, S.A. Padvi, Y.B. Wagh, D.S. Dalal, Tetrahedron Lett. 56, 2441 (2015)

    Article  CAS  Google Scholar 

  45. A. Upadhyay, L.K. Sharma, V.K. Singh, R. Dubey, N. Kumar, R.K.P. Singh, Tetrahedron Lett. 58, 1245 (2017)

    Article  CAS  Google Scholar 

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Acknowledgements

This study was supported by the Research Council of Arak University (Grant No. 94Ah.Ph.D).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Arak University, 38156-8-8349, Arāk, Iran

    Najmieh Ahadi, Mohammad Ali Bodaghifard & Akbar Mobinikhaledi

  2. Institute of Nanosciences and Nanotechnology, Arak University, 38156-88349, Arāk, Iran

    Mohammad Ali Bodaghifard

Authors
  1. Najmieh Ahadi
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  2. Mohammad Ali Bodaghifard
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  3. Akbar Mobinikhaledi
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Correspondence to Mohammad Ali Bodaghifard.

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Ahadi, N., Bodaghifard, M.A. & Mobinikhaledi, A. Preparation and characterization of a novel organic–inorganic hybrid nanostructure: application in synthesis of spirocompounds. Res Chem Intermed 46, 3277–3294 (2020). https://doi.org/10.1007/s11164-020-04130-x

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