Advertisement

Sulfonic acid-functionalized poly(4-styrenesulfonic acid) mesoporous graphene oxide hybrid for one-pot preparation of coumarin-based pyrido[2,3-d]pyrimidine-dione derivatives

  • Mohammad Hosein SayahiEmail author
  • Saeed BahadorikhaliliEmail author
  • Seyyed Jafar Saghanezhad
  • Max A. Miller
  • Mohammad Mahdavi
Article
  • 13 Downloads

Abstract

Sulfonic acid-functionalized poly(4-styrenesulfonic acid) mesoporous graphene oxide hybrid (PSSA-MGO) is prepared by polymerization of 4-styrenesulfonic acid on the surface of mesoporous graphene oxide. The catalyst is fully characterized by several methods including Fourier-transform infrared spectroscopy, Brunauer–Emmett–Teller adsorption–desorption analysis, scanning and transmission electron microscopy. PSSA-MGO is used as an efficient acidic catalyst for the one-pot preparation of some novel chromenopyridopyrimidine-dione derivatives via the three-component reaction of 4-aminocoumarin, thiobarbituric acid and aromatic aldehydes. All the obtained products were also characterized. This synthetic procedure presents some advantages including an eco-friendly procedure, high yield of the products and recyclability of the catalyst.

Keywords

Poly(4-styrenesulfonic acid) Mesoporous graphene oxide Pyridopyrimidinedione 4-aminocoumarin Multi-component reaction 

Notes

Acknowledgements

We gratefully acknowledge the support of this work by Payame Noor University (PNU).

Supplementary material

11164_2019_3962_MOESM1_ESM.pdf (704 kb)
Supplementary material 1 (PDF 704 kb)

References

  1. 1.
    L. Lloyd, Handbook of industrial catalysts (Springer Science & Business Media, New York, 2011)CrossRefGoogle Scholar
  2. 2.
    M.S. Tiwari, A.B. Gawade, G.D. Yadav, Green Chem. 19, 4 (2017)CrossRefGoogle Scholar
  3. 3.
    A.S. Amarasekara, Chem. Rev. 116, 10 (2016)CrossRefGoogle Scholar
  4. 4.
    J. Li and X. Liang. Energy Convers. Manag. 141, (2017)Google Scholar
  5. 5.
    J. Jiang, O.M. Yaghi, Chem. Rev. 115, 14 (2015)CrossRefGoogle Scholar
  6. 6.
    S. Rostamnia, E. Doustkhah, RSC Adv. 4, 54 (2014)CrossRefGoogle Scholar
  7. 7.
    K. Ganjehyan, B. Nişancı, M. Sevim, A. Daştan, Ö. Metin, Appl. Organomet. Chem. 33, 5 (2019)CrossRefGoogle Scholar
  8. 8.
    B. Nişancı, K. Ganjehyan, Ö. Metin, A. Daştan, B. Török, J. Mol. Catal. A Chem. 409, 191 (2015)CrossRefGoogle Scholar
  9. 9.
    Z.-M. Wang, W. Wang, N. Coombs, N. Soheilnia, G.A. Ozin, ACS Nano 4, 12 (2010)Google Scholar
  10. 10.
    Y. Ying, L. Sun, Q. Wang, Z. Fan, X. Peng, RSC Adv. 4, 41 (2014)Google Scholar
  11. 11.
    S.K. Maji, S. Sreejith, A.K. Mandal, X. Ma, Y. Zhao, ACS Appl. Mater. Interfaces. 6, 16 (2014)CrossRefGoogle Scholar
  12. 12.
    L. Liao, J. Zhu, X. Bian, L. Zhu, M.D. Scanlon, H.H. Girault, B. Liu, Adv. Func. Mater. 23, 42 (2013)CrossRefGoogle Scholar
  13. 13.
    T. Gan, J. Sun, K. Huang, L. Song, Y. Li, Sens. Actuators B Chem. 177, 412 (2013)CrossRefGoogle Scholar
  14. 14.
    R.P. Herrera, E. Marqués-López, Multicomponent reactions: concepts and applications for design and synthesis (John Wiley & Sons, Hoboken, 2015)Google Scholar
  15. 15.
    J. Zhu, Q. Wang, M. Wang, Multicomponent reactions in organic synthesis (John Wiley & Sons, Hoboken, 2014)CrossRefGoogle Scholar
  16. 16.
    A. Mouradzadegun, M.A. Mostafavi, M.R. Ganjali, React. Kinet. Mech. Catal. 124, 2 (2018)CrossRefGoogle Scholar
  17. 17.
    A. Bazgir, M.M. Khanaposhtani, A.A. Soorki, Bioorg. Med. Chem. Lett. 18, 21 (2008)CrossRefGoogle Scholar
  18. 18.
    E.M. Grivsky, S. Lee, C.W. Sigel, D.S. Duch, C.A. Nichol, J. Med. Chem. 23, 3 (1980)CrossRefGoogle Scholar
  19. 19.
    G. Nam, C.M. Yoon, E. Kim, C.K. Rhee, J.H. Kim, J.H. Shin, S.H. Kim, Bioorg. Med. Chem. Lett. 11, 5 (2001)CrossRefGoogle Scholar
  20. 20.
    R.E. Hackler and G.P. Jourdan, (Google Patents, 1991)Google Scholar
  21. 21.
    R.B. Tenser, A. Gaydos, K.A. Hay, Antimicrobial Agents Chemother 45, 12 (2001)CrossRefGoogle Scholar
  22. 22.
    Y.S. Sanghvi, S.B. Larson, S.S. Matsumoto, L.D. Nord, D.F. Smee, R.C. Willis, T.L. Avery, R.K. Robins, G.R. Revankar, J. Med. Chem. 32, 3 (1989)Google Scholar
  23. 23.
    S.P. Satasia, P.N. Kalaria, D.K. Raval, Org. Biomol. Chem. 12, 11 (2014)CrossRefGoogle Scholar
  24. 24.
    M.C. Pirrung, K.D. Sarma, J. Am. Chem. Soc. 126, 2 (2004)CrossRefGoogle Scholar
  25. 25.
    M.-O. Simon, C.-J. Li, Chem. Soc. Rev. 41, 4 (2012)CrossRefGoogle Scholar
  26. 26.
    S. Bahadorikhalili, A. Ashtari, L. Mamani, P.R. Ranjbar, M. Mahdavi, Appl. Organomet. Chem. 32, 4 (2018)Google Scholar
  27. 27.
    S.E. Sadat-Ebrahimi, S.M. Haghayegh-Zavareh, S. Bahadorikhalili, A. Yahya-Meymandi, M. Mahdavi, M. Saeedi, Synth. Commun. 47, 24 (2017)CrossRefGoogle Scholar
  28. 28.
    S. Bahadorikhalili and A.R. Sardarian, Polycycl Aromat Compd (2018)Google Scholar
  29. 29.
    M. Mahdavi, H. Lijan, S. Bahadorikhalili, L. Ma’mani, P.R. Ranjbar, A. Shafiee, RSC Adv 6, 34 (2016)Google Scholar
  30. 30.
    S.J. Saghanezhad, Y. Nazari, F. Davod, RSC Adv 6, 30 (2016)CrossRefGoogle Scholar
  31. 31.
    S.J. Saghanezhad, S. Sayyahi, Res Chem Intermed 43, 4 (2017)Google Scholar
  32. 32.
    M.H. Sayahi, S.J. Saghanezhad, M. Mahdavi, Res. Chem. Intermed. 44, 1 (2018)CrossRefGoogle Scholar
  33. 33.
    A.R. Kiasat, F. Chadorian, S.J. Saghanezhad, C. R. Chim. 18, 12 (2015)CrossRefGoogle Scholar
  34. 34.
    M.H. Sayahi, S. Bahadorikhalili, S.J. Saghanezhad, M. Mahdavi, Res. Chem. Intermed. 44, 9 (2018)Google Scholar
  35. 35.
    S. Bahadorikhalili, L. Ma’mani, H. Mahdavi and A. Shafiee. Microporous Mesoporous Mater. 262, (2018)Google Scholar
  36. 36.
    J. Chen, B. Yao, C. Li and G. Shi. Carbon 64, 225 (2013)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor University (PNU)TehranIran
  2. 2.School of Chemistry, College of ScienceUniversity of TehranTehranIran
  3. 3.ACECR-Production Technology Research InstituteAhvazIran
  4. 4.Polymer Chemistry Department, Ångström LaboratoryUppsala UniversityUppsalaSweden
  5. 5.Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences InstituteTehran University of Medical SciencesTehranIran

Personalised recommendations