Skip to main content
SpringerLink
Log in

The magnetic nanostructured natural hydroxyapatite (HAP/Fe3O4 NPs): an efficient, green and recyclable nanocatalyst for the synthesis of biscoumarin derivatives under solvent-free conditions

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

Abstract

The magnetic nanostructured natural hydroxyapatite (HAP/Fe3O4 NPs) as a novel magnetic nanocatalyst was synthesized and fully characterized. The excellent catalytic activity of HAP/Fe3O4 NPs was investigated in the synthesis of biscoumarin derivatives under mild, green and solvent-free conditions. A series of aromatic (bearing different functional groups), heteroaromatic and aliphatic aldehydes have been converted to biscoumarins with good to excellent isolated yields. The significant advantages offered by the present method in close agreement with green chemistry principles are: catalyst is inexpensive, non-toxic, easy handling and reusable up to six recycle runs, magnetic separation of nanostructured catalyst, simple work-up procedure, short reaction time, high yields of products and using solvent-free conditions.

Graphical abstract

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
Scheme 3
Fig. 7

Similar content being viewed by others

References

  1. J.D. Hepworth, C.D. Gabbutt, B.M. Heron, in Comprehensive Heterocyclic Chemistry-II, ed. by A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Pergamon, NewYork, 1996), p. 417

    Google Scholar 

  2. S. Li, X. Qi, B. Huang, Catal. Today 276, 139 (2016)

    Article  CAS  Google Scholar 

  3. J.C. Kim, R. Ryoo, M. Opanasenko, M. Shamzhy, J. Cejka, ACS Catal. 5, 2596 (2015)

    Article  CAS  Google Scholar 

  4. M.A. Musa, A. Zhou, O.M. Sadik, J. Med. Chem. 7, 112 (2011)

    Article  CAS  Google Scholar 

  5. K.M. Khan, Z.S. Saify, M.Z. Khan, C.M.I. Zia-Ullah, S. Atta-ur-Rahman, S. Perveen, Z.H. Chohan, C.T. Supuran, J. Enzyme Inhib. Med. Chem. 19, 373 (2004)

    Article  CAS  PubMed  Google Scholar 

  6. C.A. Kontogiorsis, D.J. Hadjipavloo-Litina, J. Med. Chem. 48, 6400 (2005)

    Article  CAS  Google Scholar 

  7. M.E. Riveiro, A. Moglioni, R. Vazquez, N. Gomez, G. Facorro, L. Piehl, E.R. de Celis, C. Shayo, C. Davio, Bioorg. Med. Chem. 16, 2665 (2008)

    Article  CAS  PubMed  Google Scholar 

  8. I. Kostova, S. Bhatia, P. Grigorov, Curr. Med. Chem. 18, 3929 (2011)

    Article  CAS  PubMed  Google Scholar 

  9. N. Hamdi, F. Bouabdallah, A. Romerosa, R. Benhassen, C. R. Chimie. 13, 1261 (2010)

    Article  CAS  Google Scholar 

  10. M. Waheed, N. Ahmed, Tetrahedron Lett. 57, 3785 (2016)

    Article  CAS  Google Scholar 

  11. W.Y. Lin, L.L. Long, W. Tan, Chem. Commun. 46, 1503 (2010)

    Article  CAS  Google Scholar 

  12. L.Q. Yan, Z.N. Kong, W. Shen, W.Q. Du, Y. Zhou, Z.J. Qi, RSC Adv. 6, 5636 (2016)

    Article  CAS  Google Scholar 

  13. S. Park, J.E. Kwon, S.H. Kim, J. Seo, K. Chung, S.Y. Park, D.J. Jang, B.M. Medina, J. Gierschner, S.Y. Park, J. Am. Chem. Soc. 131, 14043 (2009)

    Article  CAS  PubMed  Google Scholar 

  14. H.Q. Li, L. Cai, J.X. Li, Y.X. Hu, P.P. Zhou, J.M. Zhang, Dyes Pigment. 91, 309 (2011)

    Article  CAS  Google Scholar 

  15. K.D. Seo, H.M. Song, M.J. Lee, M. Pastore, C. Anselmi, F.D. Angelis, M.K. Nazeeruddin, M. Gräetzel, H.K. Kim, Dyes Pigments. 90, 304 (2011)

    Article  CAS  Google Scholar 

  16. L. Long, Y. Wu, L. Wang, A. Gong, F. Hu, C. Zhang, Chem. Commun. 51, 10435 (2015)

    Article  CAS  Google Scholar 

  17. E.B.B. Ong, N. Watanabe, A. Saito, Y. Futamura, K.H.A.E. Galil, A. Koito, N. Najimudin, H. Osada, J. Biol. Chem. 16, 14049 (2011)

    Article  CAS  Google Scholar 

  18. A.K. Shaily, N. Ahmed, Supramol. Chem. 29, 146 (2017)

    Article  CAS  Google Scholar 

  19. M. Waheed, N. Ahmed, Tetrahedron Lett. 57, 3785 (2016)

    Article  CAS  Google Scholar 

  20. P. Kalita, R. Kumar, Micropor. Mesopor Mat. 149, 1 (2012)

    Article  CAS  Google Scholar 

  21. B. Karami, M. Kiani, Catal. Commun. 14, 62 (2011)

    Article  CAS  Google Scholar 

  22. A. Mobaraki, S. Yasham, B. Movassagh, Synlett 26, 1263 (2015)

    Article  CAS  Google Scholar 

  23. D. Khan, S. Mukhtar, M.A. Alsharif, M.I. Alahmdi, N. Ahmed, Tetrahedron Lett. 58, 3183 (2017)

    Article  CAS  Google Scholar 

  24. S. Pakdel, B. Akhlaghinia, A. Mohammadinezhad, Chem. Afr. (2019)

  25. J.C. Jung, J.H. Lee, S. Oh, J.G. Lee, O.S. Park, Bioorg. Med. Chem. Lett. 14, 5527 (2004)

    Article  CAS  PubMed  Google Scholar 

  26. S. Stanchev, G. Momekov, F. Jensen, I. Manolov, Eur. J. Med. Chem. 43, 694 (2008)

    Article  CAS  PubMed  Google Scholar 

  27. I. Kostava, I. Manolov, I. Nicolova, S. Konstantonov, M. Karaivanova, Eur. J. Med. Chem. 36, 339 (2001)

    Article  Google Scholar 

  28. Z.H. Chohan, A.U. Shaikh, A. Rauf, C.T. Supuran, J. Enzyme Inhib. Med. Chem. 21, 741 (2006)

    Article  CAS  PubMed  Google Scholar 

  29. J.W. Hinman, H. Hoeksema, E.L. Caron, W.G. Jackson, J. Am. Chem. Soc. 78, 1072 (1956)

    Article  CAS  Google Scholar 

  30. J.H. Lee, H.B. Bang, S.Y. Han, J.G. Jun, Tetrahedron Lett. 48, 2889 (2007)

    Article  CAS  Google Scholar 

  31. R.D.R.S. Manian, J. Jayashankaran, R. Raghunathan, Tetrahedron Lett. 48, 1385 (2007)

    Article  CAS  Google Scholar 

  32. H. Zhao, N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, G.W. Milne, Y. Pommier, T.R. Burke, J. Med. Chem. 40, 242 (1997)

    Article  CAS  PubMed  Google Scholar 

  33. C. Montagner, S.M. De Souza, C. Groposo, F. Delle Monache, E.F.A. Smania, A. Smania Jr., Z. Naturforsch C Bio. Sci. 63, 21 (2008)

    Article  CAS  Google Scholar 

  34. Y.A. Al-Soud, H.H. Al-Sa’doni, H.A. Amajaour, K.S. Salih, M.S. Mubarak, N.A. Al-Masoudic, Z. Naturforsch., B: Chem. Sci. 63, 83 (2008)

    Article  CAS  Google Scholar 

  35. K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, M.I. Choudhary, S. Perveen, Bioorg. Med. Chem. 12, 1963 (2004)

    Article  CAS  PubMed  Google Scholar 

  36. V.D. Kancheva, P.V. Boranova, J.T. Nechev, I.I. Monolov, Biochimie 92, 1138 (2010)

    Article  CAS  PubMed  Google Scholar 

  37. A.N. Bhat, B.D. Jain, Talanta 5, 271 (1960)

    Article  CAS  Google Scholar 

  38. J.S. Yadav, V.S. Reddy, A.K. Basak, B. Visali, A.V. Narsaiah, K. Nagaiah, Eur. J. Org. Chem. 2004, 546 (2004)

    Article  CAS  Google Scholar 

  39. M.M. Heravi, F. Nahavandi, S. Sadjadi, H.A. Oskooie, F.F. Bamoharram, Synth. Commun. 40, 498 (2010)

    Article  CAS  Google Scholar 

  40. J. Albadi, A. Mansournezhad, S. Salehnasab, Res. Chem. Intermed. 41, 5713 (2015)

    Article  CAS  Google Scholar 

  41. A. Zhu, M. Wang, L. Li, J. Wang, RSC Adv. 5, 73974 (2015)

    Article  CAS  Google Scholar 

  42. K.P. Boroujeni, P. Ghasemi, Z. Rafienia, Monatsh. Chem. 145, 1023 (2014)

    Article  CAS  Google Scholar 

  43. R. Rezaei, F. Moezzi, M.M. Doroodmand, Chin. Chem. Lett. 25, 183 (2014)

    Article  CAS  Google Scholar 

  44. B. Sadeghi, J. Chem. Res. 37, 171 (2013)

    Article  CAS  Google Scholar 

  45. K. Tabataeian, H. Heidari, A. Khorshidi, M. Managhani, N.O. Mahmoodi, J. Serb. Chem. Soc. 77, 407 (2012)

    Article  CAS  Google Scholar 

  46. W. Li, Y. Wang, Z. Wang, L. Dai, Y. Wang, Catal. Lett. 141, 1651 (2011)

    Article  CAS  Google Scholar 

  47. H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7, 890 (2010)

    Article  CAS  Google Scholar 

  48. L. Shastri, S. Kalegowda, M. Kulkarni, Tetrahedron Lett. 48, 7215 (2007)

    Article  CAS  Google Scholar 

  49. N. Montazeri, V. Vahabi, Bulg. Chem. Commun. 47, 136 (2015)

    Google Scholar 

  50. M.A. Zolfigol, R. Nasrabadi, S. Baghery, Appl. Organomet. Chem. 30, 500 (2016)

    Article  CAS  Google Scholar 

  51. M. Sedighi, N. Montazeri, Adv. Stud. Biol. 7, 89 (2015)

    Article  Google Scholar 

  52. K.P. Boroujeni, S. Hadizadeh, S. Hasani, A. Fadavi, M. Shahrokh, Acta Chim. Slov. 64, 692 (2017)

    Article  CAS  Google Scholar 

  53. B. Karmakara, A. Nayakb, J. Banerji, Tetrahedron Lett. 53, 4343 (2012)

    Article  CAS  Google Scholar 

  54. F. Shirini, A. Fallah-Shojaei, L. Samavi, M. Abedini, RSC Adv. 6, 48469 (2016)

    Article  CAS  Google Scholar 

  55. S.K. Patil, D.V. Awale, M.M. Vadiyar, S.A. Patil, S.C. Bhise, S.S. Kolekar, Res. Chem. Intermed. 43, 5365 (2017)

    Article  CAS  Google Scholar 

  56. J. Safaei-Ghomi, F. Eshteghal, H. Shahbazi-Alavi, Polycycl. Aromat. Compd. 1, 1 (2017)

    Article  CAS  Google Scholar 

  57. A. Singh, P. Raj, R. Kaur, A. Singh, N. Kaur, N. Singh, New J. Chem. 41, 3872 (2017)

    Article  Google Scholar 

  58. Z. Karimi-Jaberi, M.R. Nazarifar, B. Pooladian, Chin. Chem. Lett. 23, 781 (2012)

    Article  CAS  Google Scholar 

  59. A. Shamsaddini, E. Sheikhhosseini, Int. J. Org. Chem. 4, 135 (2014)

    Article  CAS  Google Scholar 

  60. M. BenOsman, S. DialloGarcia, J. Krafft, C. Méthivier, J. Blanchard, T. Yoshiokaand, J. Kubo, Phys. Chem. Chem. Phys. 18, 27837 (2016)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  65. M. Razavi Fard, B. Akhlaghinia, J. Indian Chem. Soc. 92, 1715 (2015)

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  70. Moghadam B. Nazari, B. Akhlaghinia, S. Rezazadeh, Res. Chem. Intermed. 42, 1487 (2016)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  79. M. Esmaielpour, B. Akhlaghinia, R. Jahanshahi, J. Chem. Sci. 129, 313 (2017)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  81. M. Ghasemzadeh, B. Akhlaghinia, Bull. Chem. Soc. Jpn 90, 1119 (2017)

    Article  CAS  Google Scholar 

  82. M. Nejatianfar, B. Akhlaghinia, R. Jahanshahi, Appl. Organomet. Chem. 32, 4095 (2017)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  84. N. Mohammadian, B. Akhlaghinia, Res. Chem. Intermed. 43, 3325 (2017)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  86. A. Mohammadinezhad, B. Akhlaghinia, Aust. J. Chem. 71, 32 (2018)

    Article  CAS  Google Scholar 

  87. N. Mohammadian, B. Akhlaghinia, Res. Chem. Intermed. 44, 1085 (2018)

    Article  CAS  Google Scholar 

  88. Z. Zarei, B. Akhlaghinia, Turk. J. Chem. 42, 170 (2018)

    Article  CAS  Google Scholar 

  89. M. Ghasemzadeh, B. Akhlaghinia, Chemistry Select. 3, 3161 (2018)

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  92. N. Razavi, B. Akhlaghinia, R. Jahanshahi, Catal. Lett. 147, 360 (2017)

    Article  CAS  Google Scholar 

  93. R. Jahanshahi, B. Akhlaghinia, Catal. Lett. 147, 2640 (2017)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  95. F. Heidari, M.E. Bahrololoom, D. Vashaee, L. Tayebi, Ceram. Int. 41, 3094 (2015)

    Article  CAS  Google Scholar 

  96. M.E. Bahrololoom, M. Javidi, S. Javadpour, J. Ma, J. Ceram. Process. Res. 10, 129 (2009)

    Google Scholar 

  97. M.M.A. Nikje, L. Sarchami, L. Rahmani, Int. J. Nanosci. Nanotechnol. 11, 39 (2015)

    Google Scholar 

  98. J. Venkatesan, S.K. Kim, Materials 3, 4761 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  99. X.Y. Lü, Y.B. Fan, D. Gu, W. Cui, Key Eng. Mater. 342, 213 (2007)

    Article  Google Scholar 

  100. Z. Zhang, Z. Yuan, D. Tang, Y. Ren, K. Lv, B. Liu, Chemsuschem 7, 3496 (2014)

    Article  CAS  PubMed  Google Scholar 

  101. M.S. Sajadi, M. Meskinfam, H. Jazdarreh, Int. J. Nano. Dim. 1, 57 (2010)

    Google Scholar 

  102. S. Li, H. Bai, J. Wang, X. Jing, Q. Liu, M. Zhang, R. Chen, L. Liu, C. Jiao, Chem. Eng. J. 193, 372 (2012)

    Article  CAS  Google Scholar 

  103. R.J. Abraham, J.J. Byrne, L. Griffiths, M. Perez, Magn. Reson. Chem. 44, 491 (2006)

    Article  CAS  PubMed  Google Scholar 

  104. J.C. Lien, S.C. Chen, L.J. Huang, S.C. Kuo, J. Chin. Chem. Soc. 51, 847 (2004)

    Article  CAS  Google Scholar 

  105. G.X. Gong, J.F. Zhou, L.T. An, X.L. Duan, S.J. Ji, Synth. Commun. 39, 497 (2009)

    Article  CAS  Google Scholar 

  106. M. Nikpassand, L. Zare Fekri, S. Sahrapeima, Bull. Chem. Soc. Ethiop. 31, 323 (2017)

    Article  CAS  Google Scholar 

  107. A. Noorahmadsab Nadaf, K. Shivashankar, J. Heterocycl. Chem. 55, 1375 (2018)

    Article  CAS  Google Scholar 

  108. S.S. Kauthale, S.U. Tekale, K.M. Jadhav, R.P. Pawar, Mol. Divers 20, 763 (2016)

    Article  CAS  PubMed  Google Scholar 

  109. M.N. Elinson, A.N. Vereshchagin, O.O. Sokolova, J. Org. Chem. Part iii, 121 (2017)

    Google Scholar 

  110. A. Zhu, S. Bai, L. Li, M. Wang, J. Wang, Catal. Lett. 145, 1089 (2015)

    Article  CAS  Google Scholar 

  111. S.C. Azimi, K. Rad-Moghadam, Iran. Chem. Commun. 3, 356 (2015)

    CAS  Google Scholar 

  112. A. Sahar, Z. Ali Khan, M. Ahmad, A.F. Zahoor, A. Mansha, A. Iqbal, Trop. J. Pharm. Res. 16, 203 (2017)

    Article  CAS  Google Scholar 

  113. R. Karimian, F. Piri, A.A. Safari, S.J. Davarpanah, J. Nanostruct. 3, 52 (2013)

    Article  Google Scholar 

  114. Faisal M, F.A. Larik, A. Saeed, J. Porous Mater. (2018)

  115. V. Padalkar, K. Phatangare, S. Takale, R. Pisal, A. Chaskar, J. Saudi Chem. Soc. 19, 42 (2015)

    Article  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the partial support of this study by the Ferdowsi University of Mashhad Research Council (Grant No. 2/47664).

Author information

Authors and Affiliations

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

    Batool Akhlaghinia, Parvin Sanati, Arezou Mohammadinezhad & Zeinab Zarei

Authors
  1. Batool Akhlaghinia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Parvin Sanati
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Arezou Mohammadinezhad
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zeinab Zarei
    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 27674 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Akhlaghinia, B., Sanati, P., Mohammadinezhad, A. et al. The magnetic nanostructured natural hydroxyapatite (HAP/Fe3O4 NPs): an efficient, green and recyclable nanocatalyst for the synthesis of biscoumarin derivatives under solvent-free conditions. Res Chem Intermed 45, 3215–3235 (2019). https://doi.org/10.1007/s11164-019-03788-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-019-03788-2

Keywords

Search

Navigation