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An efficiently and quickly synthesized NiO@g-C3N4 nanocomposite-catalyzed green synthesis of spirooxindole derivatives

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Abstract

NiO@g-C3N4 as an efficient catalyst for the synthesis of spirooxindole derivatives was prepared by impregnation of g-C3N4 with NiO nanoparticles and characterized by various techniques including thermogravimetric analysis, transmission electron microscopy, X-ray diffraction and Fourier transform infrared spectroscopy. The one-pot synthesis of spirooxindole derivatives using 1 mmol isatin, 1 mmol dimedone (or 4-hydroxycoumarin or ethyl acetoacetate) and 1 mmol malononitrile was carried out in the presence of 50 mg NiO@g-C3N4 in EtOH media at reflux conditions. The results showed that both series of reactions had short reaction times (less than 7 min) and high reaction efficiency (greater than 87%). Some advantages can be cited for this method, including short reaction time, excellent yields, easy workup and a reusable and inexpensive nanocatalyst.

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References

  1. I.O. Ghinea, R.M. Dinica, New synthetic pathways, new applications, in Scope of Selective Heterocycles from Organic and Pharmaceutical Perspective, ed. by R. Varala (InTech, Rijeka, 2017), p. 115

    Google Scholar 

  2. I.V. Borovlev, O.P. Demidov, G.A. Amangasieva, E.K. Avakyan, N.A. Kurnosova, J. Heterocycl. Chem. 406, 54 (2016)

    Google Scholar 

  3. N. Azizi, E. Gholibeghlo, Z. Manocheri, Sci. Iran. 19, 574 (2012)

    Article  CAS  Google Scholar 

  4. S. Budde, J.K. Ega, B. Gavaji, R. Vadde, Int. J. Res. Appl. 2, 365 (2015)

    Google Scholar 

  5. G. Mohammadi Ziarani, R. Moradi, A. Badiei, N. Lashgari, B. Moradi, A. Abolhasani Soorki, J. Taibah Univ. Sci. 9, 555 (2015)

    Article  Google Scholar 

  6. K. Rad-Moghadama, S. Gholizadeh, IJC 4, 41 (2014)

    Google Scholar 

  7. F.X. Felpin, O. Ibarguren, L. Nassar-Hardy, E. Fouquet, J. Org. Chem. 74, 1349 (2009)

    Article  CAS  Google Scholar 

  8. J. Kothandapani, A. Ganesan, G.K. Mani, A.J. Kulandaisamy, J.B. Balaguru Rayappan, S.S. Ganesan, Tetrahedron Lett. 57, 3472 (2016)

    Article  CAS  Google Scholar 

  9. A. Allahresani, Iran. J. Catal. 7, 293 (2017)

    CAS  Google Scholar 

  10. J.A. Makawana, C.B. Sangani, Y.F. Yao, Y.T. Duan, P.C. Lv, H.L. Zhu, Mini Rev. Med. Chem. 16, 1303 (2016)

    Article  CAS  Google Scholar 

  11. M.A. Nasseri, F. Kamali, B. Zakerinasab, RSC Adv. 5, 26517 (2015)

    Article  CAS  Google Scholar 

  12. J.A. Tanna, R.G. Chaudhary, N.V. Gandhare, A.R. Rai, H.D. Juneja, IJSER 6, 93 (2015)

    Google Scholar 

  13. R.J. Kalbasi, N. Mosaddegh, Bull. Korean Chem. Soc. 32, 2584 (2011)

    Article  Google Scholar 

  14. L.L. Chng, N. Erathodiyil, J.Y. Ying, Acc. Chem. Res. 46, 1825 (2013)

    Article  CAS  Google Scholar 

  15. H. Sachdeva, D. Dwivedi, R.R. Bhattacharjee, S. Khaturia, R. Saroj, J. Chem. 2013, 1 (2013)

    Article  Google Scholar 

  16. X. Miao, X. Shen, J. Wu, Z. Ji, J. Wang, L. Kong, M. Liu, C. Song, Appl. Catal. A Gen. 539, 104 (2017)

    Article  CAS  Google Scholar 

  17. H. Liu, Z. Xu, Z. Zhang, D. Ao, Appl. Catal. A Gen. 518, 150 (2016)

    Article  CAS  Google Scholar 

  18. L. Ge, C. Han, J. Liu, Y. Li, Appl. Catal. A Gen. 409–410, 215 (2011)

    Article  Google Scholar 

  19. Q. Hao, X. Niu, C. Nie, S. Hao, W. Zou, J. Gea, D. Chen, W. Yao, Phys. Chem. Chem. Phys. 18, 31410 (2016)

    Article  CAS  Google Scholar 

  20. B. Lin, C. Xue, X. Yan, G. Yang, G. Yang, Appl. Surf. Sci. 357, 346 (2015)

    Article  CAS  Google Scholar 

  21. L.C. Chen, X.T. Zeng, P. Si, Y.M. Chen, Y.W. Chi, D.H. Kim, G. Chen, Anal. Chem. 86, 4188 (2014)

    Article  CAS  Google Scholar 

  22. A. Thomas, A. Fischer, F. Goettmann, M. Antonietti, J.-O. Müller, R. Schlogl, J.M. Carlsson, J. Mater. Chem. 18, 4893 (2008)

    Article  CAS  Google Scholar 

  23. X. Wang, K. Maeda, A. Thomas, K. Takanabe, Nat. Mater. 8, 76 (2009)

    Article  CAS  Google Scholar 

  24. B. Long, J. Lin, X. Wang, J. Mater. Chem. A 2, 2942 (2014)

    Article  CAS  Google Scholar 

  25. A. Allahresani, B. Taheri, M.A. Nasseri, Res. Chem. Intermed. 44, 6979 (2018)

    Article  CAS  Google Scholar 

  26. A. Allahresani, B. Taheri, M.A. Nasseri, Res. Chem. Intermed. 44, 1173 (2018)

    Article  CAS  Google Scholar 

  27. A. Allahresani, M.A. Nasseri, A. Nakhaei, Res. Chem. Intermed. 43, 6367 (2017)

    Article  CAS  Google Scholar 

  28. S. Riyaz, A. Indrasena, A. Naidu, P.K. Dubey, Indian J. Chem. B 53, 1442 (2014)

    Google Scholar 

  29. 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 

  30. C. Wu, R. Shen, J. Chen, C. Hu, Bull. Korean Chem. Soc. 34, 2431 (2013)

    Article  CAS  Google Scholar 

  31. S.P. Satasia, P.N. Kalaria, J.R. Avalani, D.K. Raval, Tetrahedron 70, 5763 (2014)

    Article  CAS  Google Scholar 

  32. P. Rai, M. Srivastava, J. Singh, J. Singh, New J. Chem. 38, 3181 (2014)

    Article  CAS  Google Scholar 

  33. A. Hasaninejad, N. Golzar, M. Beyrati, A. Zare, M.M. Doroodmand, J. Mol. Catal. A Chem. 372, 137 (2013)

    Article  CAS  Google Scholar 

  34. L.-M. Wang, N. Jiao, J. Qiu, J.-J. Yu, J.-Q. Liu, F.-L. Guo, Y. Liu, Tetrahedron 66, 339 (2010)

    Article  CAS  Google Scholar 

  35. M.N. Elinson, R.F. Nasybullin, F.V. Ryzhkov, T.A. Zaimovskaya, G.I. Nikishi, Monatsh. Chem. 146, 631 (2015)

    Article  CAS  Google Scholar 

  36. S.J. Chai, Y.F. Lai, J.C. Xu, H. Zheng, Q. Zhu, P.F. Zhang, Advanc. Synth. Catal. 353, 371 (2011)

    Google Scholar 

  37. L. Zhao, B. Zhou, Y. Li, Heteroatom Chem. 22, 673 (2011)

    Google Scholar 

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Acknowledgements

The authors are grateful to the University of Birjand and Payam Noor University of Mashhad for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Payam Noor University, Mashhad, Iran

    Zahra Amini Moqadam & Hassan Hassani

  2. Department of Chemistry, Faculty of Sciences, University of Birjand, P.O. Box 97175-615, Birjand, Iran

    Ali Allahresani

Authors
  1. Zahra Amini Moqadam
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  2. Ali Allahresani
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  3. Hassan Hassani
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Correspondence to Hassan Hassani.

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Amini Moqadam, Z., Allahresani, A. & Hassani, H. An efficiently and quickly synthesized NiO@g-C3N4 nanocomposite-catalyzed green synthesis of spirooxindole derivatives. Res Chem Intermed 46, 299–311 (2020). https://doi.org/10.1007/s11164-019-03951-9

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