Skip to main content

Advertisement

SpringerLink
Log in

Highly efficient and environmentally benign method for the synthesis of tetrahydrobenzo[b]pyrans using Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 as a new bio- and nanocatalyst with Brønsted base and Lewis acid properties

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

Abstract

Nanosized Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 was used as a biocatalyst for the synthesis of tetrahydrobenzo[b]pyrans derivatives via one-pot three-component reaction of various aldehydes, dimedone and malononitrile. The reactions were easily carried out at 60 °C under mild and heterogeneous conditions. The catalyst was easily synthesized by high-energy ball milling, and the effect of some parameters such as specific surface area, pore volume, particle size, pH and crystallinity degree of the catalyst on the yield and reaction time was studied. The catalyst showed both Brønsted base and Lewis acid properties. The acidic sites were determined by FT-IR spectroscopy of the pyridine adsorption technique at different temperatures. Using a biocatalyst and an environmentally benign procedure, good to high yields of the products and short reaction time were the advantages of the method.

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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 2
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. M. Mazaheri, M. Haghighatzadeh, A.M. Zahedi, S.K. Sadrnezhaad, J. Alloys Compd. 471(180), 180 (2009)

    Article  CAS  Google Scholar 

  2. H. Arami, M. Mohajerani, M. Mazloumi, R. Khalifehzadeh, A. Lak, S.K. Sadrnezhaad, J. Alloys Compd. 469, 391 (2009)

    Article  CAS  Google Scholar 

  3. M. Descamps, J.C. Hornez, A. Leriche, J. Eur. Ceram. Soc. 29, 369 (2009)

    Article  CAS  Google Scholar 

  4. Y. Chen, X. Miao, Ceram. Int. 30, 1961 (2004)

    Article  CAS  Google Scholar 

  5. J. Wang, Y. Chao, Q. Wan, Z. Zhu, H. Yu, Acta Biomater. 5, 1798 (2009)

    Article  CAS  Google Scholar 

  6. N.Y. Mostafa, H.M. Hassan, F.H. Mohamed, J. Alloys Compd. 479, 692 (2009)

    Article  CAS  Google Scholar 

  7. M. Turkoza, A.O. Atillab, Z. Evisc, Ceram. Int. 39, 8925 (2013)

    Article  Google Scholar 

  8. B. Basar, A. Tezcaner, D. Keskin, Z. Evis, Ceram. Int. 36, 1633 (2010)

    Article  CAS  Google Scholar 

  9. M.H. Fathi, E. Mohammadi Zahrani, J. Cryst. Growth 311, 1392 (2009)

    Article  CAS  Google Scholar 

  10. Y. Chen, X. Miao, Biomaterials 26, 1205 (2005)

    Article  CAS  Google Scholar 

  11. H. Eslami, M. Solati-Hashjin, M. Tahriri, Mater. Sci. Eng. C 29, 1387 (2009)

    Article  CAS  Google Scholar 

  12. H. Kim, H.E. Kim, J.C. Knowles, Biomaterials 25, 3351 (2004)

    Article  CAS  Google Scholar 

  13. H. Kim, Y. Kong, C. Bae, Y. Noh, H. Kim, Biomaterials 25, 2919 (2004)

    Article  CAS  Google Scholar 

  14. N. Johari, M.H. Fathi, M.A. Golozar, Ceram. Int. 37, 3247 (2011)

    Article  CAS  Google Scholar 

  15. W.L. Suchanek, K. Byrappa, P. Shuk, R.E. Riman, V.F. Janas, K.S. TenHuisen, Biomaterials 25, 4647 (2004)

    Article  CAS  Google Scholar 

  16. W. Mroz, A. Bombalska, S. Burdynska, M. Jedynski, A. Prokopiuk, B. Budner, A. Slosarczyk, A. Zima, E. Menaszek, A. Scisłowska-Czarnecka, K. Niedzielski, J. Mol. Struct. 977, 145 (2010)

    Article  CAS  Google Scholar 

  17. T.J. Webster, C. Ergun, R.H. Doremus, R. Bizios, J. Biomed. Mater. Res. 59(2), 312 (2002)

    Article  CAS  Google Scholar 

  18. Z.P. Sun, B. Ercan, Z. Evis, T.J. Webster, J. Biomed. Mater. Res. 94A, 806 (2010)

    CAS  Google Scholar 

  19. M. Kheradmandfard, M.H. Fathi, J. Alloys Compd. 504, 141 (2010)

    Article  CAS  Google Scholar 

  20. Y. Cai, S. Zhang, X. Zeng, Y. Wang, M. Qian, W. Weng, Thin Solid Films 517, 5347 (2009)

    Article  CAS  Google Scholar 

  21. A.E. Portera, N. Patela, J.N. Skepper, S.M. Best, W. Bonfield, Biomaterials 24, 4609 (2003)

    Article  Google Scholar 

  22. A. Balamurugan, A.H.S. Rebelo, A.F. Lemos, J.H.G. Rocha, J.M.G. Ventura, J.M.F. Ferreira, Dent. Mater. 24, 1374 (2008)

    Article  CAS  Google Scholar 

  23. N. Hijon, M.V. Cabanas, J. Pena, M. Vallet-Regi, Acta Biomater. 2, 567 (2006)

    Article  Google Scholar 

  24. A.E. Porter, N. Patel, J.N. Skepper, S.M. Best, W. Bonfield, J. Biomater. 24, 4609 (2003)

    Article  CAS  Google Scholar 

  25. A. Aminian, M. Solati-Hashjin, A. Samadikuchaksaraei, F. Bakhshi, F. Gorjipour, A. Farzadi, F. Moztarzadeh, M. Schmucker, Ceram. Int. 37, 1219 (2011)

    Article  CAS  Google Scholar 

  26. T. Ahmadia, A. Monshi, V. Mortazavi, M.H. Fathi, S. Sharifi, B. HashemiBeni, A. MoghareAbed, M. Kheradmandfard, A. Sharifnabi, Ceram. Int. 40, 8341 (2014)

    Article  Google Scholar 

  27. C.V. Ragel, M. Vallet-Regí, L.M. Rodríguez-Lorenzo, Biomaterials 23, 1865 (2002)

    Article  CAS  Google Scholar 

  28. M.H. Fathi, E.M. Zahrani, Iran. J. Pharm. Res. 4, 209 (2008)

    Google Scholar 

  29. A.M. El-Agrody, M.H. El-Hakium, M.S. Abdel-Latif, A.H. Fekry, E.S.M. El-Sayed, K.A. El-Gareab, Acta Pharm. 50, 111 (2000)

    CAS  Google Scholar 

  30. T. Narender, S. Shweta Gupta, Bioorg. Med. Chem. Lett. 14, 3913 (2004)

    Article  CAS  Google Scholar 

  31. L. Lakshmi, K. Pandey, A. Kapil, N. Singh, M. Samant, A. Dube, Phytomedicine 14, 36 (2007)

    Article  CAS  Google Scholar 

  32. L. Alvey, S. Prado, V. Huteau, B. Saint-Jonis Michel, S. Koch, S.M. Cole, F.T. Tillequin, Y.L. Janin, Bioorg. Med. Chem. 16, 8264 (2008)

    Article  CAS  Google Scholar 

  33. D. Kumar, V.B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 44, 3805 (2009)

    Article  CAS  Google Scholar 

  34. T. Symeonidis, M. Chamilos, D.J. Hadjipavlou-Litina, M. Kallitsakis, K.E. Litinas, Bioorg. Med. Chem. Lett. 19, 1139 (2009)

    Article  CAS  Google Scholar 

  35. M. Mahdavi, J. Davoodi, M.R. Zali, A. Foroumadi, Biomed. Pharmacother. 65, 175 (2011)

    Article  CAS  Google Scholar 

  36. S.A. Patil, J. Wang, X.S. Li, J. Chen, T.S. Jones, A. Hosni-Ahmed, R. Patil, W.L. Seibel, W. Li, D.D. Miller, Bioorg. Med. Chem. Lett. 22, 4458 (2012)

    Article  CAS  Google Scholar 

  37. M.M. Kandeel, A.M. Kamal, E.K. Abdelall, H.A.H. Elshemy, Eur. J. Med. Chem. 59, 183 (2013)

    Article  CAS  Google Scholar 

  38. Z. Saffari, H. Aryapour, A. Akbarzadeh, A. Foroumadi, N. Jafari, M.F. Zarabi, A. Farhangi, Tumor Biol. 35, 5845 (2014)

    Article  CAS  Google Scholar 

  39. W. Zhu, C. Chen, C. Sun, S. Xu, C. Wu, F. Lei, H. Xia, Q. Tu, P. Zhenge, Eur. J. Med. Chem. 93, 64 (2015)

    Article  CAS  Google Scholar 

  40. C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F.W. Keana, P.C.T. Int, Appl. WO 0075123 (2000). Chem. Abstr. 134, 29313a (2001)

    Google Scholar 

  41. G. Kaupp, M.R. Naimi-Jamal, J. Schmeyers, Tetrahedron 59, 3753 (2003)

    Article  CAS  Google Scholar 

  42. N. Martin, C. Pascual, C. Seoane, J. Soto, Heterocycle 26, 2811 (1987)

    Article  CAS  Google Scholar 

  43. M.H. Enagdi, R.M. Abdel-Motaleb, M. Mustafa, M.F. Zayed, E.M. Kamel, J. Heterocycl. Chem. 24, 1677 (1987)

    Article  Google Scholar 

  44. R.M. Shaker, Pharmazie 51, 148 (1996)

    CAS  Google Scholar 

  45. X.Z. Lian, Y. Huang, Y.Q. Li, W.J. Zheng, Monatsh. Chem. 139, 129 (2008)

    Article  CAS  Google Scholar 

  46. M. Amirnejad, M.R. Naimi-Jamal, H. Tourani, H. Ghafuri, Monatsh. Chem. 144, 1219 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  48. X.S. Wang, D.Q. Shi, S.J. Tu, C.S. Yao, Synth. Commun. 33, 119 (2003)

    Article  CAS  Google Scholar 

  49. J.T. Li, W.Z. Xu, L.C. Yang, T.S. Li, Synth. Commun. 34, 4565 (2004)

    Article  CAS  Google Scholar 

  50. A. Hasaninejad, M. Shekouhy, N. Golzar, A. Zare, M.M. Doroodmand, Appl. Catal. A Gen. 402, 11 (2011)

    Article  CAS  Google Scholar 

  51. A. Rostami, B. Atashkar, H. Gholami, Catal. Commun. 37, 69 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  53. E. Chandralekha, A. Thangamani, R. Valliappan, Res. Chem. Intermed. 41, 1951 (2015)

    Article  CAS  Google Scholar 

  54. R. Hekmatshoar, S. Majedi, K. Bakhtiari, Catal. Commun. 9, 307 (2008)

    Article  CAS  Google Scholar 

  55. M.M. Khodaei, K. Bahrami, A. Farrokhi, Synth. Commun. 40, 578 (2010)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  57. F. Noorisadeh, M.T. Maghsoodlou, N. Hazeri, M. Kangani, Res. Chem. Intermed. 41, 5907 (2015)

    Article  Google Scholar 

  58. Y. Ren, W. Zhang, J. Lu, K. Gao, X. Liao, X. Chen, RSC Adv. 5, 79405 (2015)

    Article  CAS  Google Scholar 

  59. M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)

    Article  CAS  Google Scholar 

  60. H. Sheibani, M. Seifi, A. Bazgir, Synth. Commun. 39, 1055 (2009)

    Article  CAS  Google Scholar 

  61. M. Abdollahi-Alibeik, N. Sadeghi-Vasafi, React. Kinet. Mech. Catal. 112, 511 (2014)

    Article  CAS  Google Scholar 

  62. B. Maleki, N. Nasiri, R. Tayebee, A. Khojastehnezhad, H.A. Akhlaghi, RSC Adv. 6, 79128 (2016)

    Article  CAS  Google Scholar 

  63. A. Khazaei, F. Gholami, V. Khakyzadeh, A.R. Moosavi-Zare, J. Afsar, RSC Adv. 5, 14305 (2015)

    Article  CAS  Google Scholar 

  64. M.A. Nasseri, S.M. Sadeghzadeh, Monatsh. Chem. 144, 1551 (2013)

    Article  CAS  Google Scholar 

  65. M. Khoobi, L. Mamani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal. A Chem. 359, 74 (2012)

    Article  CAS  Google Scholar 

  66. B. Tyagi, C.D. Chudasama, R.V. Jasra, Appl. Clay Sci. 31, 16 (2006)

    Article  CAS  Google Scholar 

  67. D. Almahrouqi, J. Vinogradov, M.D. Jackson, Adv. Colloid Interface Sci. 240, 60 (2017)

    Article  CAS  Google Scholar 

  68. A. Doostmohammadi, A. Monshi, R. Salehi, M.H. Fathi, Z. Golniya, A.U. Daniels, Ceram. Int. 37, 2311 (2011)

    Article  CAS  Google Scholar 

  69. T.L. Ho, Hard and Soft Acid and Bases Principle in Organic Chemistry (Academic Press, New York, 1977)

    Google Scholar 

  70. F.A. Carey, R.J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, 3rd edn. (Plenum Press, New York, 1990)

    Book  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the funding support received for this project from the Islamic Azad University, Khorasgan, and fasa Branches.

Author information

Authors and Affiliations

  1. Department of Science, Isfahan (Khorasgan) Branch, Islamic Azad University, Isfahan, 81595-158, Iran

    Leila Khazdooz

  2. Department of Science, Fasa Branch, Islamic Azad University, PO Box No. 364, Fasa, Fars, 7461713591, Iran

    Amin Zarei

  3. Department of Materials Engineering, Shahreza Branch, Islamic Azad University, Shahreza, Isfahan, 311-86145, Iran

    Tahmineh Ahmadi

  4. Department of Chemistry, Shahreza Branch, Islamic Azad University, Shahreza, Isfahan, 311-86145, Iran

    Hamidreza Aghaei & Laleh Golestanifar

  5. Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, PO Box No. 517, Najafabad, Isfahan, 8514143131, Iran

    Nafisehsadat Sheikhan

Authors
  1. Leila Khazdooz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amin Zarei
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tahmineh Ahmadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hamidreza Aghaei
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Laleh Golestanifar
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Nafisehsadat Sheikhan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Leila Khazdooz.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khazdooz, L., Zarei, A., Ahmadi, T. et al. Highly efficient and environmentally benign method for the synthesis of tetrahydrobenzo[b]pyrans using Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 as a new bio- and nanocatalyst with Brønsted base and Lewis acid properties. Res Chem Intermed 44, 93–115 (2018). https://doi.org/10.1007/s11164-017-3092-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-017-3092-3

Keywords

Search

Navigation