Skip to main content
Log in

Fibrous nanosilica spheres KCC-1@NH2 as highly effective and easily retrievable catalyst for the synthesis of chromenes

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

Abstract

A three-component reaction of naphthalene-1,5-diol, malononitrile and aromatic aldehydes has been achieved in the presence of fibrous nanosilica spheres KCC-1@NH2 as highly effective heterogeneous catalysts to produce of chromenes. In this study, simple and effective methods were used for the preparation of nanosilica spheres KCC-1@NH2 as basic catalysts. A fibrous surface morphology, high surface area, high mechanical stability, the easy separation of the nanocatalyst and the recyclability, nontoxicity, versatility, combined with low reaction times and excellent yields, make the present protocol very useful for the synthesis of the chromenes. The catalyst has been characterized by FT-IR, XRD, EDX, FE-SEM, TEM, BET and TGA. Also, the synthesized products were confirmed by 1H-NMR, 13C-NMR, FT-IR.

Graphical abstract

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.

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

Similar content being viewed by others

References

  1. M.S.L. Kumar, J. Singh, S.K. Manna, S. Maji, R. Konwar, G. Panda, Bioorg. Med. Chem. Lett. 28, 778 (2018)

    Article  CAS  Google Scholar 

  2. A.M. Abdella, Y. Moatasim, M.A. Ali, A.H.M. Elwahy, I.A. Abdelhamid, J. Heterocycl. Chem. 54, 1854 (2017)

    Article  CAS  Google Scholar 

  3. M. Kidwai, S. Saxena, M.K.R. Khan, S.S. Thukral, Bioorg. Med. Chem. Lett. 15, 4295 (2005)

    Article  CAS  PubMed  Google Scholar 

  4. E. Menteşe, N. Baltaş, O. Bekircan, Arch. Pharm. 352, 1900227 (2019)

    Article  CAS  Google Scholar 

  5. P. Iniyavan, S. Sarveswari, V. Vijayakumar, Res. Chem. Intermed. 41, 7413–7426 (2015)

    Article  CAS  Google Scholar 

  6. A.J. Johnson, A. Kumar, S.A. Rasheed, S.P. Chandrika, A. Chandrasekhar, S. Baby, A. Subramoniam, J. Ethnopharmacol. 130, 267 (2010)

    Article  CAS  PubMed  Google Scholar 

  7. V.T. Angelova, Y. Voynikov, P. Andreeva-Gateva, S. Surcheva, N. Vassilev, T. Pencheva, J. Tchekalarova, Med. Chem. Res. 26, 1884 (2017)

    Article  CAS  Google Scholar 

  8. H.R. Shaterian, M. Mohammadnia, J. Mol. Liq. 177, 353 (2013)

    Article  CAS  Google Scholar 

  9. M. Curini, F. Epifano, S. Chimichi, F. Montanari, M. Nocchetti, O. Rosati, Tetrahedron Lett. 46, 3497 (2005)

    Article  CAS  Google Scholar 

  10. J.M. Khurana, B. Nand, P. Saluja, Tetrahedron 66, 5637 (2010)

    Article  CAS  Google Scholar 

  11. M. Zendehdel, M.A. Bodaghifard, H. Behyar, Z. Mortezaei, Microporous Mesoporous Mater. 266, 83 (2018)

    Article  CAS  Google Scholar 

  12. M.M. Heravi, B. Baghernejad, H.A. Oskooie, J. Chin. Chem. Soc. 55, 659 (2008)

    Article  CAS  Google Scholar 

  13. M. Kangani, N. Hazeri, M.T. Maghsoodlou, J. Chin. Chem. Soc. 63, 896 (2016)

    Article  CAS  Google Scholar 

  14. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  15. Y.M. Ren, C. Cai, Catal. Commun. 9, 1017 (2008)

    Article  CAS  Google Scholar 

  16. Y.L. Shi, M. Shi, Org. Lett. 7, 3057 (2005)

    Article  CAS  PubMed  Google Scholar 

  17. M.T. Maghsoodlou, N. Hazeri, M. Lashkari, F.N. Shahrokhabadi, B. Naghshbandi, M.S. Kazemi-doost, M. Rashidi, F. Mir, M. Kangani, S. Salahi, Res. Chem. Intermed. 41, 6985 (2015)

    Article  CAS  Google Scholar 

  18. S. Mohammadi, Z. Mohammadi, J. Compos. Compd. 3, 84 (2021)

    Google Scholar 

  19. S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48, 3299 (2007)

    Article  CAS  Google Scholar 

  20. N. Majumdar, N.D. Paul, S. Mandal, B. Bruin, W.D. Wulff, ACS Catal. 5, 2329 (2015)

    Article  CAS  Google Scholar 

  21. R. Pratap, V.J. Ram, Chem. Rev. 114, 10476 (2014)

    Article  CAS  PubMed  Google Scholar 

  22. V. Polshettiwar, J. Thivolle-Cazat, M. Taoufik, F. Stoffelbach, S. Norsic, J.M. Basset, Angew. Chem. Int. Ed. 50, 2747–2751 (2011)

    Article  CAS  Google Scholar 

  23. F. Zarei, A. Marjani, R. Soltani, Eur. Polym. J. 119, 400–409 (2019)

    Article  CAS  Google Scholar 

  24. A. Fihri, D. Cha, M. Bouhrara, N. Almana, V. Polshettiwar, Chem. Sus. Chem. 5, 85 (2012)

    Article  CAS  Google Scholar 

  25. Z. Dong, X. Le, X. Li, W. Zhang, C. Dong, J. Ma, Appl. Catal. B 158–159, 129 (2014)

    Article  CAS  Google Scholar 

  26. A. Fihri, M. Bouhrara, U. Patil, D. Cha, Y. Saih, V. Polshettiwar, ACS Catal. 2, 1425 (2012)

    Article  CAS  Google Scholar 

  27. Z.N. Siddiqui, K. Khan, N. Ahmed, Catal. Lett. 144, 623 (2014)

    Article  CAS  Google Scholar 

  28. S.M. Sadeghzadeh, J. Mol. Catal. A Chem. 423, 216 (2016)

    Article  CAS  Google Scholar 

  29. S.M. Sadeghzadeh, RSC Adv. 6, 75973 (2016)

    Article  CAS  Google Scholar 

  30. S. Azizi, N. Shadjou, M. Hasanzadeh, Nanocomposites 5, 124 (2019)

    Article  CAS  Google Scholar 

  31. S.M. Sadeghzadeh, R. Zhiani, M. Moradi, ChemistrySelect 3, 3516 (2018)

    Article  CAS  Google Scholar 

  32. R. Zhiani, S.M. Sadeghzadeh, S. Emrani, RSC Adv. 8, 6259 (2018)

    Article  CAS  Google Scholar 

  33. V. Polshettiwar, D. Cha, X. Zhang, J.M. Basset, Angew. Chem. Int. Ed. 49, 9652 (2010)

    Article  CAS  Google Scholar 

  34. B. Singh, V. Polshettiwar, J. Mater. Chem. A 4, 7005 (2016)

    Article  CAS  Google Scholar 

  35. S.N. Bukhari, C.C. Chong, H.D. Setiabudi, Y.W. Cheng, L.P. The, A.A. Jalil, Chem. Eng. Sci. 229, 116141 (2021)

    Article  CAS  Google Scholar 

  36. P. Gautam, M. Dhiman, V. Polshettiwar, B.M. Bhanage, Green Chem. 18, 5890 (2016)

    Article  CAS  Google Scholar 

  37. R.S. Varma, R. Dahiya, J. Org. Chem. 63, 8038 (1998)

    Article  CAS  Google Scholar 

  38. S.M. Sadeghzadeh, R. Zhiania, S. Emrania, RSC Adv. 7, 24885 (2017)

    Article  CAS  Google Scholar 

  39. X. Huang, Z. Tao, J.C. Praskavich, A. Goswami Jr., J.F. Al-Sharab, T. Minko, V. Polshettiwar, T. Asefa, Langmuir 30, 10886 (2014)

    Article  CAS  PubMed  Google Scholar 

  40. Z. Sun, D. Guo, L. Zhang, H. Li, B. Yanga, S. Yan, J. Mater. Chem. B. 3, 3201 (2015)

    Article  CAS  PubMed  Google Scholar 

  41. M.E. Davis, Nature 417, 813 (2002)

    Article  CAS  PubMed  Google Scholar 

  42. A. Corma, H. Garcia, Top. Catal. 48, 8 (2008)

    Article  CAS  Google Scholar 

  43. S. Verma, M. Nandi, A. Modak, S.L. Jain, A. Bhaumik, Adv. Synth. Catal. 353, 1897 (2011)

    Article  CAS  Google Scholar 

  44. A. Christian, W. Veronika, B. Christoph, B. Thomas, Chem. Mater. 26, 435 (2014)

    Article  CAS  Google Scholar 

  45. J.G. Huddleston, A.E. Visser, W.M. Reichert, H.D. Willauer, G.A. Brokera, R.D. Rogers, Green Chem. 3, 156 (2001)

    Article  CAS  Google Scholar 

  46. S. Azizi, J. Soleymani, M. Hasanzadeh, Nanocomposites 6, 31 (2020)

    Article  CAS  Google Scholar 

  47. Z.S. Ershad, N. Shadjou, M. Mahmoudian, F. Ahour, J. Environ. Chem. Eng. 9, 105329 (2021)

    Article  CAS  Google Scholar 

  48. M. Anvari Gharabaghlou, N. Shadjou, A. Poursattar Marjani, Appl. Organomet. Chem. 34, 5868 (2020)

    Article  CAS  Google Scholar 

  49. N. Bayal, B. Singh, R. Singh, V. Polshettiwar, Sci. Rep. 6, 24888 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. N. Khantan, N. Shadjou, M. Hasanzadeh, Nanocomposites 5, 104 (2019)

    Article  CAS  Google Scholar 

  51. F. Alemi-Tameh, J. Safaei-Ghomi, M. Mahmoudi Hashemi, R. Teymuri, Res. Chem. Intermed. 42, 6391 (2016)

    Article  CAS  Google Scholar 

  52. J. Safaei-Ghomi, S. Zahedi, Appl. Organomet. Chem. 29, 566 (2015)

    Article  CAS  Google Scholar 

  53. H.S. Oboudatian, J. Safaei-Ghomi, Sci. Rep. 12, 1 (2022)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to University of Kashan for supporting this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Javad Safaei-Ghomi.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 35 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Oboudatian, H.S., Safaei-Ghomi, J. Fibrous nanosilica spheres KCC-1@NH2 as highly effective and easily retrievable catalyst for the synthesis of chromenes. Res Chem Intermed 48, 2069–2085 (2022). https://doi.org/10.1007/s11164-022-04695-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-022-04695-9

Keywords

Navigation