Advertisement

Organic base grafted on magnetic nanoparticles as a recoverable catalyst for the green synthesis of hydropyridine rings

  • 10 Accesses

Abstract

Synthesis of 4-aminiquinaldine grafted on silica-coated nano-Fe3O4 particles (MNPs-AQ) and their performance as a retrievable heterogeneous basic catalyst are disclosed. The catalytic performance of this novel material was studied for the green synthesis of substituted 1,4-dihydropyridine and polyhydroquinoline derivatives via one-pot multicomponent reactions. Eco-friendly method, high yield and purity of the desired products, and short reaction time along with the ease of the work-up procedure outline the advantages of these new methodologies over the earlier ones. The surface and magnetic properties of the core/shell hybrid nanoparticles were characterized via TEM, SEM, XRD, EDS, and FT-IR analysis techniques. This nanocatalyst is recyclable without any deterioration in its catalytic activity.

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

Access options

Buy single article

Instant unlimited access to the full article PDF.

US$ 39.95

Price includes VAT for USA

Subscribe to journal

Immediate online access to all issues from 2019. Subscription will auto renew annually.

US$ 199

This is the net price. Taxes to be calculated in checkout.

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

References

  1. 1.

    G. Swarnalatha, G. Prasanthi, N. Sirisha, C.M. Chetty, Int. J. ChemTech Res. 3, 75 (2011)

  2. 2.

    G.M. Reddy, M. Shiradkar, A.K. Chakravarthy, Curr. Org. Chem. 11, 847 (2007)

  3. 3.

    M. Inouye, T. Mio, K. Sumino, Eur. J. Clin. Pharmacol. 56, 35 (2000)

  4. 4.

    C.O. Wilson, J.M. Beale, J.H. Block, Wilson, Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry (Lippincott Williams & Wilkins, Baltimore, 2011)

  5. 5.

    J. Briede, D. Daija, M. Stivrina, G. Duburs, Cell Biochem. Funct. 17, 89 (1999)

  6. 6.

    G.L. Bird, A.T. Prach, A.D. McMahon, J.A. Forrest, P.R. Mills, B.J. Danesh, J. Hepatol. 28, 194 (1998)

  7. 7.

    S. Cihat, S. Rahime, Mini-Rev. Med. Chem. 6, 747 (2006)

  8. 8.

    A. Hantzsch, Justus Liebigs Ann. Chem. 215, 1 (1882)

  9. 9.

    C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957 (2004)

  10. 10.

    J.P. Wan, Y. Liu, RSC Adv. 2, 9763 (2012)

  11. 11.

    R. Surasani, D. Kalita, A.V.D. Rao, K. Yarbagi, K.B. Chandrasekhar, J. Fluor. Chem. 135, 91–96 (2012)

  12. 12.

    A. Kumar, R.A. Maurya, Tetrahedron 63(9), 1946–1952 (2007)

  13. 13.

    S.A. Kotharkar, R.R. Nagawade, D.B. Shinde, Ukr. Bioorg. Acta 1, 3–5 (2006)

  14. 14.

    J. Safari, S.H. Banitaba, S.D. Khalili, J. Mol. Catal. A Chem. 335, 46–50 (2011)

  15. 15.

    F.M. Tamaddon, S. Moradi, J. Mol. Catal. A Chem. 370, 117–122 (2013)

  16. 16.

    S. Ko, C.-F. Yao, Tetrahedron 62(31), 7293–7299 (2006)

  17. 17.

    S. Ko, M.N.V. Sastry, C. Lin, C.F. Yao, Tetrahedron Lett. 46(34), 5771–5774 (2005)

  18. 18.

    J.D. Akbari, S.D. Tala, M.F. Dhaduk, H.S. Joshi, Arkivoc xii, 126–135 (2008)

  19. 19.

    L.M. Wang, J. Sheng, L. Zhang, J.W. Han, Z. Fan, H. Tian, C.T. Qian, Tetrahedron 61(6), 1539–1543 (2005)

  20. 20.

    A.G. Sathicq, G.P. Romanelli, A. Ponzinibbio, G.T. Baronetti, H.J. Thomas, Lett. Org. Chem. 7, 511 (2010)

  21. 21.

    S.-J. Ji, Z.-Q. Jiang, J. Lu, T.-P. Loh, Synlett 5, 831–835 (2004)

  22. 22.

    M. Li, W.-S. Guo, L.-R. Wen, Y.-F. Li, H.-Z. Yang, J. Mol. Catal. A Chem. 258(1–2), 133–138 (2006)

  23. 23.

    R. Sridhar, P.T. Perumal, Tetrahedron 61(9), 2465–2470 (2005)

  24. 24.

    G. Sabitha, G.S.K.K. Reddy, C.S. Reddy, J.S. Yadav, Tetrahedron Lett. 44(21), 4129–4131 (2003)

  25. 25.

    M. Lei, L. Ma, L. Hu, Synth. Commun. 41(13), 1969–1976 (2011)

  26. 26.

    D. Bandyopadhyay, S. Maldonado, B.K. Banik, Molecules 17, 2643–2662 (2012)

  27. 27.

    A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 50(37), 5248–5250 (2009)

  28. 28.

    D.S. Rekunge, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett. 58(12), 1240–1244 (2017)

  29. 29.

    M.A. Bodaghifard, M. Hamidinasab, N. Ahadi, Curr. Org. Chem. 22(3), 234–267 (2018)

  30. 30.

    L. Han, S.W. Park, D.W. Park, Energ. Environ. Sci. 2, 1286 (2009)

  31. 31.

    L. Han, H.J. Choi, S.J. Choi, B. Liu, D.W. Park, Green Chem. 13, 1023 (2011)

  32. 32.

    B. Rác, A. Molnar, P. Forgo, M. Mohai, I. Bertóti, J. Mol. Catal. A Chem. 244, 46 (2006)

  33. 33.

    M.A. Nasseri, M. Sadeghzadeh, J. Chem. Sci. 125, 537 (2013)

  34. 34.

    V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)

  35. 35.

    S. Shylesh, V. Schünemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 3428 (2010)

  36. 36.

    A. Farrokhi, K. Ghodrati, I. Yavari, Catal. Commun. 63, 41 (2015)

  37. 37.

    J. Safari, Z. Abedi-Jazini, Z. Zarnegar, M. Sadeghi, J. Nanopart. Res. 17, 1 (2015)

  38. 38.

    S. Rostamnia, M. Amini, J. Nanopart. Res. 16, 1 (2014)

  39. 39.

    Y. Leng, K. Sato, Y. Shi, J.G. Li, T. Ishigaki, T. Yoshida, H. Kamiya, J. Phys. Chem. C 113, 16681 (2009)

  40. 40.

    A.L. Morel, S.I. Nikitenko, K. Gionnet, A. Wattiaux, J. Lai-Kee-Him, C. Labrugere, B. Chevalier, G. Deleris, C. Petibois, A. Brisson, ACS Nano 2, 847 (2008)

  41. 41.

    M.A. Bodaghifard, A. Mobinikhaledi, S. Asadbegi, Appl. Organomet. Chem. 31, e3557 (2017). https://doi.org/10.1002/aoc.3557

  42. 42.

    M.A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. Soc. 14, 365–376 (2017)

  43. 43.

    S. Asadbegi, M.A. Bodaghifard, A. Mobinikhaledi, Res. Chem. Intermed. (2017). https://doi.org/10.1007/s11164-017-3200-4

  44. 44.

    K. Can, M. Ozmen, M. Ersoz, Colloids Surf B Biointerfaces 71(1), 154–159 (2009)

  45. 45.

    W. Stöber, A. Fink, E. Bohn, J. Colloid Interface Sci. 26, 62 (1968)

  46. 46.

    M.K. Marchewka, Mater. Sci. Eng. B 95(3), 214–221 (2002)

  47. 47.

    G. Feng, D. Hu, L. Yang, Y. Cui, X.-A. Cui, H. Li, Sep. Purif. Technol. 74(2), 253–260 (2010)

  48. 48.

    J. Giri, S.G. Thakurta, J. Bellare, A.K. Nigam, D. Bahadur, J. Magn. Magn. Mater. 293(1), 62–68 (2005)

  49. 49.

    K. Petcharoen, A. Sirivat, Mat. Sci. Eng. B 177, 421 (2012)

  50. 50.

    J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, A. Ziarati, Chin. Chem. Lett. 24, 921 (2013)

  51. 51.

    J. Marco-Contelles, R. León, C. de Los Ríos, A. Guglietta, J. Terencio, M.G. López, A.G. García, M. Villarroya, J. Med. Chem. 49, 7607 (2006)

  52. 52.

    J. Marco-Contelles, R. León, C. de Los Ríos, A. Samadi, M. Bartolini, V. Andrisano, O. Huertas, X. Barril, F.J. Luque, M.I. Rodríguez-Franco, B. López, M.G. López, A.G. García, M. do Carmo Carreiras, M. Villarroya, J. Med. Chem. 52, 2724 (2009)

  53. 53.

    X. He, Y. Shang, Z. Yu, M. Fang, Y. Zhou, G. Han, F. Wu, J. Org. Chem. 79, 8882 (2014)

  54. 54.

    R. León, C. de Los Ríos, J. Marco-Contelles, M.G. López, A.G. García, M. Villarroya, Eur. J. Med. Chem. 43, 668 (2008)

  55. 55.

    A.M. Zonouz, D. Moghani, Synth. Commun. 41, 2152 (2011)

  56. 56.

    M. Hajjami, B. Tahmasbi, RSC Adv. 5, 59194 (2015)

  57. 57.

    M. Hong, C. Cai, W.B. Yi, J. Fluor. Chem. 131(1), 111 (2010)

Download references

Acknowledgements

The authors gratefully acknowledge the financial support from the Research Council of Arak University (Grant No. 95/5330).

Author information

Correspondence to Mohammad Ali Bodaghifard.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 69 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Bodaghifard, M.A. Organic base grafted on magnetic nanoparticles as a recoverable catalyst for the green synthesis of hydropyridine rings. J IRAN CHEM SOC 17, 483–492 (2020) doi:10.1007/s13738-019-01788-y

Download citation

Keywords

  • 1,4-Dihydropyridines
  • Polyhydroquinoline
  • Green chemistry
  • Hybrid nanoparticles