Skip to main content
Log in

Preparation and characterization of MNPs–PhSO3H as a heterogeneous catalyst for the synthesis of benzo[b]pyran and pyrano[3,2-c]chromenes

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this study, an efficient and novel procedure has been reported for loading sulfanilic acid on the surface of magnetite Fe3O4 nanoparticles using tris(hydroxymethyl) aminomethane and 1,2-dichloroethane. Next, the synthesized nanocatalyst was fully characterized using FT-IR, XRD, TGA, VSM, SEM, and TEM. The results show that the synthesis of magnetic nanocatalyst has been successful with a range of 2–20 nm in size. Finally, the catalytic activity of this superparamagnetic nanocatalyst was explored for the synthesis of tetrahydrobenzo[b]pyran and 2-amino-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile derivatives. The synthesized nanocatalyst has advantages such as non-toxicity, short reaction time, easy workup, cleaner reaction profiles under mild reaction conditions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 3
Scheme 4
Fig. 9

Similar content being viewed by others

References

  1. L. Chen, A. Noory Fajer, Z. Yessimbekov, M. Kazemi, M. Mohammadi, J. Sulfur Chem. 40, 451 (2019)

    CAS  Google Scholar 

  2. A. Ghorbani-Choghamarani, M. Mohammadi, Z. Taherinia, J. Iran. Chem. Soc. 16, 411 (2019)

    CAS  Google Scholar 

  3. A. Ghorbani-Choghamarani, M. Mohammadi, T. Tamoradi, M. Ghadermazi, Polyhedron 158, 25 (2019)

    CAS  Google Scholar 

  4. M. Kazemi, M. Ghobadi, A. Mirzaie, Nanotechnol. Rev. 7, 43 (2018)

    CAS  Google Scholar 

  5. M. Schulz‐Dobrick, I. Schnell, Open Chem. 3, SI1 (2007)

    Google Scholar 

  6. A. Ghorbani-Choghamarani, M. Mohammadi, R.H.E. Hudson, T. Tamoradi, Appl. Organomet. Chem. 33, e4977 (2019)

    Google Scholar 

  7. F. Chen, S. Xie, X. Huang, X. Qiu, J. Hazard. Mater. 322, 152 (2017)

    CAS  PubMed  Google Scholar 

  8. J. Ke, J. Liu, H. Sun, H. Zhang, X. Duan, P. Liang, X. Li, M.O. Tade, S. Liu, S. Wang, Appl. Catal. B-Environ. 200, 47 (2017)

    CAS  Google Scholar 

  9. Z. Wen, Y. Zhang, Y. Wang, L. Li, R. Chen, Chem. Eng. J. 312, 39 (2017)

    CAS  Google Scholar 

  10. F. He, J. Luo, S. Liu, Chem. Eng. J. 294, 362 (2016)

    CAS  Google Scholar 

  11. Z.W. Seh, J. Kibsgaard, C.F. Dickens, I. Chorkendorff, J.K. Nørskov, T.F. Jaramillo, Science 355, eaad4998 (2017)

    PubMed  Google Scholar 

  12. J. Shi, Chem. Rev. 113, 2139 (2013)

    CAS  PubMed  Google Scholar 

  13. J. Wang, R. Nie, L. Xu, X. Lyu, X. Lu, Green Chem. 21, 314 (2019)

    CAS  Google Scholar 

  14. G. Li, H. Yang, H. Zhang, Z. Qi, M. Chen, W. Hu, L. Tian, R. Nie, W. Huang, ACS Catal. 8, 8396 (2018)

    CAS  Google Scholar 

  15. X. Duan, J. Liu, J. Hao, L. Wu, B. He, Y. Qiu, J. Zhang, Z. He, J. Xi, S. Wang, Carbon 130, 806 (2018)

    CAS  Google Scholar 

  16. D. Wang, J. Liu, J. Xi, J. Jiang, Z. Bai, Appl. Surf. Sci 489, 477 (2019)

  17. J. Xi, H. Sun, D. Wang, Z. Zhang, X. Duan, J. Xiao, F. Xiao, L. Liu, S. Wang, Appl. Catal. B-Environ. 225, 291 (2018)

    CAS  Google Scholar 

  18. A. Tokarev, J. Yatvin, O. Trotsenko, J. Locklin, S. Minko, Adv. Funct. Mater. 26, 3761 (2016)

    CAS  Google Scholar 

  19. S.Z. Li, W. Zhang, M.H. So, C.M. Che, R.M. Wang, R. Chen, J. Mol. Catal. A-Chem. 359, 81 (2012)

    CAS  Google Scholar 

  20. W.T. Hu, B.C. Liu, Q. Wang, Y. Liu, Y.X. Liu, P. Jing, S.L. Yu, L.X. Liu, J. Zhang, Chem. Commun. 49, 7596 (2013)

    CAS  Google Scholar 

  21. Z.P. Wen, Y.L. Zhang, Y. Wang, L.N. Li, R. Chen, Chem. Eng. J. 312, 39 (2017)

    CAS  Google Scholar 

  22. A. Abo Markeb, A. Alonso, A.D. Dorado, A. Sànchez, X. Font, Environ. Technol. 37, 2099 (2016)

    CAS  PubMed  Google Scholar 

  23. M. Seifan, A. Ebrahiminezhad, Y. Ghasemi, A.K. Samani, A. Berenjian, Appl. Microbiol. Biotechnol. 102, 175 (2018)

    CAS  PubMed  Google Scholar 

  24. P. Biehl, M. Von der Lühe, S. Dutz, F.H. Schacher, Polymer 10, 91 (2018)

    Google Scholar 

  25. W. Fu, H. Yang, S. Liu, M. Li, G. Zou, Mater. Lett. 60, 1728 (2006)

    CAS  Google Scholar 

  26. S. Taheri, H. Veisi, M. Hekmati, New J. Chem. 41, 5075 (2017)

    CAS  Google Scholar 

  27. K.S. Pandit, P.V. Chavan, U.V. Desai, M.A. Kulkarni, P.P. Wadgaonkar, New J. Chem. 39, 4452 (2015)

    CAS  Google Scholar 

  28. W.A. Bubb, H.A. Berthon, P.W. Kuchel, Bioorg. Chem. 23, 119 (1995)

    CAS  Google Scholar 

  29. T.S. Jin, A.Q. Wang, X. Wang, J.S. Zhang, T.S. Li, Synlett 05, 0871 (2004)

    Google Scholar 

  30. A. Jamshidi, B. Maleki, F.M. Zonoz, R. Tayebee, Mater. Chem. Phys. 209, 46 (2018)

    CAS  Google Scholar 

  31. B. Maleki, M. Baghayeri, S.A.J. Abadi, R. Tayebee, A. Khojastehnezhad, RSC Adv. 6, 96644 (2016)

    CAS  Google Scholar 

  32. S.F. Hojati, N. MoeiniEghbali, S. Mohamadi, T. Ghorbani, Org. Prep. Proced. Int. 50, 408 (2018)

    CAS  Google Scholar 

  33. H. Sharma, S. Srivastava, RSC Adv. 8, 38974 (2018)

    CAS  Google Scholar 

  34. M. Hajjami, F. Gholamian, R.H. Hudson, A.M. Sanati, Catal. Lett. 149, 228 (2019)

    CAS  Google Scholar 

  35. H. Alinezhad, M. Tarahomi, B. Maleki, A. Amiri, Appl. Organomet. Chem. 33, e4661 (2019)

    Google Scholar 

  36. K.K. Krishnan, V.V. Dabholkar, A. Gopinathan, R. Jaiswar, J. Chem. Chem. Sci. 8, 66 (2018)

    Google Scholar 

  37. M. Norouzi, D. Elhamifar, R. Mirbagheri, Z. Ramazani, J. Taiwan Inst. Chem. Eng. 89, 234 (2018)

    CAS  Google Scholar 

  38. M. Norouzi, D. Elhamifar, Catal. Lett. 149, 619 (2019)

    CAS  Google Scholar 

  39. M.A. Shaikh, M. Farooqui, S. Abed, Res. Chem. Intermed. 45, 1595 (2019)

    CAS  Google Scholar 

  40. M. Gholamhosseini-Nazari, S. Esmati, K.D. Safa, A. Khataee, R. Teimuri-Mofrad, Res. Chem. Intermed. 45, 1841 (2019)

    CAS  Google Scholar 

  41. M. Esmaeilpour, J. Javidi, F. Dehghani, F.N. Dodeji, RSC Adv. 5, 26625 (2015)

    CAS  Google Scholar 

  42. B. Shitole, N. Shitole, M. Shingare, G. Kakde, Curr. Chem. Lett. 5, 137 (2016)

    Google Scholar 

  43. D.S. Patel, J.R. Avalani, D.K. Raval, J. Saudi Chem. Soc. 20, S401 (2016)

    CAS  Google Scholar 

  44. S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, M. Norouzi, M. Moein, Res. Chem. Intermed. 41, 8665 (2015)

    CAS  Google Scholar 

  45. D. Elhamifar, Z. Ramazani, M. Norouzi, R. Mirbagheri, J. Colloid Interface Sci. 511, 392 (2018)

    CAS  PubMed  Google Scholar 

  46. J. Yang, S. Liu, H. Hu, S. Ren, A. Ying, Chin. J. Chem. Eng. 23, 1416 (2015)

    CAS  Google Scholar 

  47. H. Hu, F. Qiu, A. Ying, J. Yang, H. Meng, Int. J. Mol. Sci. 15, 6897 (2014)

    CAS  PubMed  PubMed Central  Google Scholar 

  48. J. Davarpanah, A.R. Kiasat, S. Noorizadeh, M. Ghahremani, J. Mol. Catal. A-Chem. 376, 78 (2013)

    CAS  Google Scholar 

  49. F. Adibian, A.R. Pourali, B. Maleki, M. Baghayeri, A. Amiri, Polyhedron 175, 114179 (2019)

    Google Scholar 

  50. F. Ataie, A. Davoodnia, A. Khojastehnezhad, Polycycl. Aromat. Compd. 1 (2019)

  51. E. Mollashahi, M. Nikraftar, J. Saudi Chem. Soc 22, 42 (2018)

    CAS  Google Scholar 

  52. B. Maleki, Org. Prep. Proced. Int. 48, 3 (2016)

    Google Scholar 

Download references

Acknowledgements

The authors gratefully appreciate the partial support from the Research Council of University of Sistan and Baluchestan.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Nourallah Hazeri.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2011 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Faroughi Niya, H., Hazeri, N., Rezaie Kahkhaie, M. et al. Preparation and characterization of MNPs–PhSO3H as a heterogeneous catalyst for the synthesis of benzo[b]pyran and pyrano[3,2-c]chromenes. Res Chem Intermed 46, 1685–1704 (2020). https://doi.org/10.1007/s11164-019-04056-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-019-04056-z

Keywords

Navigation