Skip to main content
SpringerLink
Log in

Magnetic calcined oyster shell functionalized with taurine immobilized on β-cyclodextrin (Fe3O4/COS@β-CD-SO3H NPs) as green and magnetically reusable nanocatalyst for efficient and rapid synthesis of spirooxindoles

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

Abstract

Magnetic calcined oyster shell functionalized with taurine immobilized on β-cyclodextrin (Fe3O4/COS@β-CD-SO3H NPs) was prepared as a new stable, long-lived, highly efficient, and exceptional reusable magnetic nanostructured catalyst. The as-prepared solid acidic catalyst was characterized by various spectroscopic and microscopic techniques such as Fourier-transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD) analysis, scanning electron microscopy (SEM), energy-dispersive X-ray (EDX) spectroscopy, transmission electron microscopy (TEM), vibrating-sample magnetometry (VSM), thermogravimetric analysis (TGA)/differential thermogravimetry (DTG), and elemental (CHNS) analysis. The results clearly showed that the synthesized superparamagnetic catalyst existed as uniform spheres with average particle size of 16–25 nm. The new magnetic nanocatalyst (Fe3O4/COS@β-CD-SO3H NPs) was found to be very effective in one-pot multi-component reaction of isatin, active methylene component, and 1,3-dicarbonyl compounds for rapid preparation of spirooxindoles with fused chromenes in water in excellent yield. The most promising features of the presented approach are the short reaction time (15–22 min), magnetic separation of the nanostructured catalyst, simple work-up procedure, reusability of the catalyst for at least eight successive runs without any appreciable loss of activity, and high product yields (about 94–98%). Surprisingly, the present methodology proved to be environmentally sustainable, low cost, and industrially profitable for scale-up and commercialization.

Graphical abstract

A novel and green approach for synthesis of spirooxindoles using a green, inexpensive, and efficient nanocatalyst was investigated.

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

Access this article

Log in via an institution

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
Scheme 3
Fig. 8

Similar content being viewed by others

References

  1. K. Ding, Y. Lu, Z. Nikolovska-Coleska, G. Wang, S. Qiu, S. Shangary, W. Gao, D. Qin, J. Stuckey, K. Krajewski, P.P. Roller, S. Wang, J. Med. Chem. 49, 3432 (2006)

    Article  CAS  PubMed  Google Scholar 

  2. C.V. Galliford, K.A. Scheidt, Angew. Chem. Int. Ed. 46, 8748 (2007)

    Article  CAS  Google Scholar 

  3. C. Konkoy, D. Fick, S. Cai, N. Lan, J. Keana, in Chem. Abst. (2001), p. 29313a

  4. M. Zhang, Q.-Y. Fu, G. Gao, H.-Y. He, Y. Zhang, Y.-S. Wu, Z.-H. Zhang, ACS Sustain. Chem. Eng. 5, 6175 (2017)

    Article  CAS  Google Scholar 

  5. S.-L. Zhu, S.-J. Ji, Y. Zhang, Tetrahedron 63, 9365 (2007)

    Article  CAS  Google Scholar 

  6. Y.M. Litvinov, V.Y. Mortikov, A.M. Shestopalov, ACS Comb. Sci. 10, 741 (2008)

    CAS  Google Scholar 

  7. M. Kidwai, A. Jain, V. Nemaysh, R. Kumar, P.M. Luthra, Med. Chem. Res. 22, 2717 (2013)

    Article  CAS  Google Scholar 

  8. S. Gao, C.H. Tsai, C. Tseng, C.-F. Yao, Tetrahedron 64, 9143 (2008)

    Article  CAS  Google Scholar 

  9. M. Dabiri, M. Bahramnejad, M. Baghbanzadeh, Tetrahedron 65, 9443 (2009)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. D.R. Chandam, A.G. Mulik, D.R. Patil, M.B. Deshmukh, Res. Chem. Intermed. 42, 1411 (2016)

    Article  CAS  Google Scholar 

  12. A. Dandia, V. Parewa, A.K. Jain, K.S. Rathore, Green Chem. 13, 2135 (2011)

    Article  CAS  Google Scholar 

  13. 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 

  14. K. Rad-Moghadam, L. Youseftabar-Miri, Tetrahedron 67, 5693 (2011)

    Article  CAS  Google Scholar 

  15. B. Sadeghi, M. Ghasemi Pirbaluti, P. Farokhi Nezhad, R. Abbasi Nezhad, Res. Chem. Intermed. 41, 4047 (2015)

    Article  CAS  Google Scholar 

  16. G. Mohammadi Ziarani, A. Badiei, S. Mousavi, N. Lashgari, A. Shahbazi, Chin. J. Catal. 33, 1832 (2012)

    Article  CAS  Google Scholar 

  17. F. Mohamadpour, M.T. Maghsoodlou, R. Heydari, M. Lashkari, Res. Chem. Intermed. 42, 7841 (2016)

    Article  CAS  Google Scholar 

  18. C. Bodhak, A. Kundu, A. Pramanik, RSC Adv. 5, 85202 (2015)

    Article  CAS  Google Scholar 

  19. B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 5004 (2012)

    Article  CAS  Google Scholar 

  20. R.-Y. Guo, P. Wang, G.-D. Wang, L.-P. Mo, Z.-H. Zhang, Tetrahedron 69, 2056 (2013)

    Article  CAS  Google Scholar 

  21. M. Daraie, Y.S. Beheshtiha, M.M. Heravi, Monatsh. Chem. Chem. Mon. 146, 191 (2015)

    Article  CAS  Google Scholar 

  22. R. Ghahremanzadeh, Z. Rashid, A.H. Zarnani, H. Naeimi, Appl. Catal. A 467, 270 (2013)

    Article  CAS  Google Scholar 

  23. A.R. Karimi, M. Sourinia, Z. Dalirnasab, M. Karimi, Can. J. Chem. 93, 546 (2015)

    Article  CAS  Google Scholar 

  24. A.R. Karimi, R. Davood Abadi, Z. Dalirnasab, Res. Chem. Intermed. 41, 7427 (2015)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  26. B. Maheshwar Rao, G.N. Reddy, T.V. Reddy, B.L.A.P. Devi, R.B.N. Prasad, J.S. Yadav, B.V.S. Reddy, Tetrahedron Lett. 54, 2466 (2013)

    Article  CAS  Google Scholar 

  27. A. Thakur, M. Tripathi, U.C. Rajesh, D.S. Rawat, RSC Adv. 3, 18142 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. S.S.E. Ghodsinia, B. Akhlaghinia, RSC Adv. 5, 49849 (2015)

    Article  CAS  Google Scholar 

  30. S.S.E. Ghodsinia, B. Akhlaghinia, R. Jahanshahi, RSC Adv. 6, 63613 (2016)

    Article  CAS  Google Scholar 

  31. R. Jahanshahi, B. Akhlaghinia, RSC Adv. 5, 104087 (2015)

    Article  CAS  Google Scholar 

  32. R. Jahanshahi, B. Akhlaghinia, RSC Adv. 6, 29210 (2016)

    Article  CAS  Google Scholar 

  33. E. Karimian, B. Akhlaghinia, S.S.E. Ghodsinia, J. Chem. Sci. 128, 429 (2016)

    Article  CAS  Google Scholar 

  34. S.M. Masjed, B. Akhlaghinia, M. Zarghani, N. Razavi, Aust. J. Chem. 70, 33 (2017)

    Article  CAS  Google Scholar 

  35. N. Mohammadian, B. Akhlaghinia, Res. Chem. Intermed. 43, 22 (2017)

    Article  CAS  Google Scholar 

  36. N. Razavi, B. Akhlaghinia, RSC Adv. 5, 12372 (2015)

    Article  CAS  Google Scholar 

  37. N. Razavi, B. Akhlaghinia, New J. Chem. 40, 447 (2016)

    Article  CAS  Google Scholar 

  38. N.Y. Siavashi, B. Akhlaghinia, M. Zarghani, Res. Chem. Intermed. 42, 5789 (2016)

    Article  CAS  Google Scholar 

  39. Z. Zarei, B. Akhlaghinia, Chem. Pap. 69, 1421 (2015)

    Article  CAS  Google Scholar 

  40. Z. Zarei, B. Akhlaghinia, RSC Adv. 6, 106473 (2016)

    Article  CAS  Google Scholar 

  41. M. Zarghani, B. Akhlaghinia, Appl. Organomet. Chem. 29, 683 (2015)

    Article  CAS  Google Scholar 

  42. M. Zarghani, B. Akhlaghinia, RSC Adv. 5, 87769 (2015)

    Article  CAS  Google Scholar 

  43. M. Zarghani, B. Akhlaghinia, RSC Adv. 6, 31850 (2016)

    Article  CAS  Google Scholar 

  44. M. Zarghani, B. Akhlaghinia, RSC Adv. 6, 38592 (2016)

    Article  CAS  Google Scholar 

  45. M. Zarghani, B. Akhlaghinia, Bull. Chem. Soc. Jpn. 89, 1192 (2016)

    Article  CAS  Google Scholar 

  46. R. Jahanshahi, B. Akhlaghinia, Chem. Pap. 71, 1351 (2017)

    Article  CAS  Google Scholar 

  47. S.S.E. Ghodsinia, B. Akhlaghinia, Green Chem. (2019). https://doi.org/10.1039/C8GC03931C

    Article  Google Scholar 

  48. M.S. Ghasemzadeh, B. Akhlaghinia, New J. Chem. 43, 5341 (2019)

    Article  CAS  Google Scholar 

  49. S. Pakdel Asgarabad, B, Akhlaghinia, A. Mohammadinezhad, Chem. Africa 1 (2019)

  50. H. Karimzadegan, B. Akhlaghinia, M.S. Ghasemzadeh, Iran. J. Catal. (2019) (in press)

  51. M. Zamani, B. Akhlaghinia, A. Mohammadinezhad, ChemistrySelect 3, 9431 (2018)

    Article  CAS  Google Scholar 

  52. B. Akhlaghinia, P. Sanati, A. Mohammadinezhad, Z. Zareie, Res. Chem. Intermed. 45, 3215 (2019)

    Article  CAS  Google Scholar 

  53. A. Mohammadinezhad, B. Akhlaghinia, Green Chem. 19, 5625 (2017)

    Article  CAS  Google Scholar 

  54. Z. Zarei, B. Akhlaghinia, New J. Chem. 41, 15485 (2017)

    Article  CAS  Google Scholar 

  55. R. Jahanshahi, B. Akhlaghinia, New J. Chem. 41, 7203 (2017)

    Article  CAS  Google Scholar 

  56. N. Mohammadian, B. Akhlaghinia, Res. Chem. Intermed. 44, 18 (2018)

    Article  CAS  Google Scholar 

  57. R. Jahanshahi, B. Akhlaghinia, Res. Chem. Intermed. 44, 2451 (2018)

    Article  CAS  Google Scholar 

  58. M. Nejatianfar, B. Akhlaghinia, R. Jahanshahi, Appl. Organomet. Chem. 32, 4095 (2018)

    Article  CAS  Google Scholar 

  59. A. Mohammadinezhad, B. Akhlaghinia, Aust. J. Chem. 71, 32 (2017)

    Article  CAS  Google Scholar 

  60. A. Schätz, M. Hager, O. Reiser, Adv. Funct. Mater. 19, 2109 (2009)

    Article  CAS  Google Scholar 

  61. M. Zhang, Y.-H. Liu, Z.-R. Shang, H.-C. Hu, Z.-H. Zhang, Catal. Commun. 88, 39 (2017)

    Article  CAS  Google Scholar 

  62. M.-N. Chen, L.-P. Mo, Z.-S. Cui, Z.-H. Zhang, Curr. Opin. Green Sustain. Chem. 15, 27 (2019)

    Article  Google Scholar 

  63. M. Zhang, P. Liu, Y.-H. Liu, Z.-R. Shang, H.-C. Hu, Z.-H. Zhang, RSC Adv. 6, 106160 (2016)

    Article  CAS  Google Scholar 

  64. S. Sobhani, R. Jahanshahi, New J. Chem. 37, 1009 (2013)

    Article  CAS  Google Scholar 

  65. Q. Li, G. Tang, X. Xiong, Y. Cao, L. Chen, F. Xu, H. Tan, Sens. Actuators B Chem. 215, 86 (2015)

    Article  CAS  Google Scholar 

  66. M. Arana, S.E. Jacobo, H. Troiani, P.G. Bercoff, IEEE Trans. Magn. 49, 4547 (2013)

    Article  CAS  Google Scholar 

  67. B. Tural, N. Özkan, M. Volkan, J. Phys. Chem. Solids 70, 860 (2009)

    Article  CAS  Google Scholar 

  68. A.P. Herrera, M. Rodriguez, M. Torres-Lugo, C. Rinaldi, J. Mater. Chem. 18, 855 (2008)

    Article  CAS  Google Scholar 

  69. Z. Durmus, H. Kavas, M.S. Toprak, A. Baykal, T.G. Altınçekiç, A. Aslan, A. Bozkurt, S. Coşgun, J. Alloys Compd. 484, 371 (2009)

    Article  CAS  Google Scholar 

  70. H. Wei, N. Insin, J. Lee, H.-S. Han, J.M. Cordero, W. Liu, M.G. Bawendi, Nano Lett. 12, 22 (2012)

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  72. H.R. Safaei, M. Shekouhy, S. Rahmanpur, A. Shirinfeshan, Green Chem. 14, 1696 (2012)

    Article  CAS  Google Scholar 

  73. J. Zhou, Z. Dong, H. Yang, Z. Shi, X. Zhou, R. Li, Appl. Surf. Sci. 279, 360 (2013)

    Article  CAS  Google Scholar 

  74. M. Osada, C. Miura, Y.S. Nakagawa, M. Kaihara, M. Nikaido, K. Totani, Carbohydr. Polym. 92, 1573 (2013)

    Article  CAS  PubMed  Google Scholar 

  75. F.G. Pearson, R.H. Marchessault, C.Y. Liang, J. Polym. Sci. 43, 101 (1960)

    Article  Google Scholar 

  76. G. Vidal-Valat, J.P. Vidal, K. Kurki-Suonio, Acta Crystallogr. A 34, 594 (1978)

    Article  Google Scholar 

  77. H. Okudera, K. Kihara, T. Matsumoto, Acta Crystallogr. B 52, 450 (1996)

    Article  Google Scholar 

  78. G.H. Du, Z.L. Liu, X. Xia, Q. Chu, S.M. Zhang, J. Sol-Gel. Sci. Technol. 39, 285 (2006)

    Article  CAS  Google Scholar 

  79. A. Khalafi-Nezhad, S. Mohammadi, ACS Comb. Sci. 15, 512 (2013)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge partial support of this study by Ferdowsi University of Mashhad Research Council (Grant no. 3/43388).

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, 9177948974, Iran

    Narges Mohammadian & Batool Akhlaghinia

Authors
  1. Narges Mohammadian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Batool Akhlaghinia
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Batool Akhlaghinia.

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 5612 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mohammadian, N., Akhlaghinia, B. Magnetic calcined oyster shell functionalized with taurine immobilized on β-cyclodextrin (Fe3O4/COS@β-CD-SO3H NPs) as green and magnetically reusable nanocatalyst for efficient and rapid synthesis of spirooxindoles. Res Chem Intermed 45, 4737–4756 (2019). https://doi.org/10.1007/s11164-019-03860-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-019-03860-x

Keywords

Search

Navigation