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Preparation of a dual-functionalized fumed silica nanoparticle catalysis for synthesis of azaluorenone derivatives

  • Maedeh Bagheri
  • Parisa GholamzadehEmail author
  • Ghodsi Mohammadi Ziarani
  • Alireza Badiei
Article

Abstract

A dual-functional silica-based catalyst was prepared by treating fumed silica with amino-containing silane then 1,4-butane sultone. The presence of functional groups on the surface of the prepared amino sulfonic acid fumed silica (FSi–PrNH–Bu–SO3H) was confirmed by Fourier-transform infrared (FT-IR) spectroscopy. Energy-dispersive X-ray (EDX) elemental analysis showed the presence of S, N, C, O, and Si on the surface of the catalyst. The size of the agglomerated particles was observed to lie in the range of 30–50 nm by scanning electron microscopy (SEM). Finally, thermogravimetric analysis (TGA) revealed that the amount of organic compounds grafted on the surface of FSi–PrNH2 and FSi–PrNH–BuSO3H was 2.59 and 1.12 mmol/g, respectively. After well characterizing the FSi–PrNH–BuSO3H, it was used to catalyze the reaction of 1,3-indandione, isatin, ethyl acetoacetate, and ammonium acetate for synthesis of azafluorenone derivatives.

Graphical abstract

Keywords

Fumed silica Sultone Azafluorenone Nanoparticle Indandione Multicomponent 

Notes

Acknowledgements

We gratefully acknowledge the financial support from the Research Council of Alzahra University and the University of Tehran.

Compliance with ethical standards

Conflict of interest

There are no conflicts of interest to declare.

Supplementary material

11164_2019_3740_MOESM1_ESM.docx (490 kb)
Supplementary material 1 (DOCX 489 kb)

References

  1. 1.
    C.R. Schnell, S.M.L. Hamblyn, K. Hengartner, M. Wissler, Powder Technol. 20, 15 (1978)CrossRefGoogle Scholar
  2. 2.
    D. Zhang, J. Su, X. Ma, H. Tian, Tetrahedron 64, 8515 (2008)CrossRefGoogle Scholar
  3. 3.
    H. Barthel, M. Dreyer, T. Gottschalk-Gaudig, E. Nikitina Organosilicon Chemistry Set: From Molecules to Materials. (Wiley, New York, 2008)Google Scholar
  4. 4.
    P. Gholamzadeh, G. Mohammadi Ziarani, F. Zandi, A. Abolhasani Soorki, A. Badiei, F. Yazdian, C. R. Chim. 20, 833 (2017)CrossRefGoogle Scholar
  5. 5.
    H. Barthel, Colloids Surf. A 101, 217 (1995)CrossRefGoogle Scholar
  6. 6.
    J.S. Lim, S.M. Hong, D.K. Kim, S.S. Im, J. Appl. Polym. Sci. 107, 3598 (2008)CrossRefGoogle Scholar
  7. 7.
    B.C. Hong, M.S. Hallur, J.H. Liao, Synth. Commun. 36, 1521 (2006)CrossRefGoogle Scholar
  8. 8.
    C. Mérienne, G.J. Arango, D. Cortes, B.K. Cassels, A. Cavé, Phytochemistry 26, 2093 (1987)CrossRefGoogle Scholar
  9. 9.
    D. Mueller, R.A. Davis, S. Duffy, V.M. Avery, D. Camp, R.J. Quinn, J. Nat. Prod. 72, 1538 (2009)CrossRefGoogle Scholar
  10. 10.
    J.H.G. Lago, M.H. Chaves, M.C.C. Ayres, D.G. Agripino, M.C.M. Young, Planta Med. 73, 292 (2007)CrossRefGoogle Scholar
  11. 11.
    D. Addla, Bhima, B. Sridhar, A. Devi, S. Kantevari, Bioorg. Med. Chem. Lett. 22, 7475 (2012)CrossRefGoogle Scholar
  12. 12.
    S. Dhara, A. Ahmed, S. Nandi, S. Baitalik, J.K. Ray, Tetrahedron Lett. 54, 63 (2013)CrossRefGoogle Scholar
  13. 13.
    J.K. Laha, K.P. Jethava, S. Patel, K.V. Patel, J. Org. Chem. 82, 76 (2016)CrossRefGoogle Scholar
  14. 14.
    S. Tu, B. Jiang, H. Jiang, Y. Zhang, R. Jia, J. Zhang, Q. Shao, C. Li, D. Zhou, L. Cao, Tetrahedron 63, 5406 (2007)CrossRefGoogle Scholar
  15. 15.
    T. Ahmadi, G. Mohammadi Ziarani, P. Gholamzadeh, H. Mollabagher, Tetrahedron Asymmetry 28, 708 (2017)CrossRefGoogle Scholar
  16. 16.
    G. Mohammadi Ziarani, P. Gholamzadeh, A. Badiei, V. Fathi Vavsari, Res. Chem. Intermed. 44, 277 (2018)CrossRefGoogle Scholar
  17. 17.
    G. Mohammadi Ziarani, Z. Kazemi Asl, P. Gholamzadeh, A. Badiei, M. Afshar, Appl. Organomet. Chem. 31, e3830 (2017)CrossRefGoogle Scholar
  18. 18.
    P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, Biocatal. Biotransform. 35, 131 (2017)CrossRefGoogle Scholar
  19. 19.
    G. Mohammadi Ziarani, Z. Kazemi Asl, P. Gholamzadeh, A. Badiei, M. Afshar, J. Sol Gel Sci. Technol. 85, 103 (2018)CrossRefGoogle Scholar
  20. 20.
    A. Feiz, G.I. Shakibaei, Z. Yasaei, H.R. Khavasi, A. Bazgir, Helv. Chim. Acta 94, 1628 (2011)CrossRefGoogle Scholar
  21. 21.
    N.C. Dige, D.M. Pore, Synth. Commun. 45, 2498 (2015)CrossRefGoogle Scholar
  22. 22.
    A. Mondal, B. Banerjee, A. Bhaumik, C. Mukhopadhyay, ChemCatChem 8, 1185 (2016)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of ChemistryAlzahra UniversityTehranIran
  2. 2.School of Chemistry, College of ScienceUniversity of TehranTehranIran

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