Research on Chemical Intermediates

, Volume 43, Issue 2, pp 829–841 | Cite as

Silica nanosphere–graphene oxide (SiO2–GO) hybrid catalyzed facile synthesis of functionalized quinoxaline derivatives

  • Praveen V. Shitre
  • Rajkumar R. Harale
  • Bhaskar R. Sathe
  • Murlidhar S. ShingareEmail author


Herein, fabrication of spherical SiO2 nanoparticles (5 ± 0.2 nm) with uniform size is followed by their homogeneous distribution on graphene oxide (SiO2–GO) by using a simple in situ one-step method. These as synthesized catalytic materials are further characterized by transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIR), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), and others. This spectroscopic characterization demonstrated that GO acted as a good supportive substrate for controlling the size and activity of SiO2 nanospheres with their cooperation towards catalytic reactions. The optimized hybrid exhibited high catalytic activity for the synthesis of functionalized quinoxalines. Significantly, the as-synthesised SiO2–GO nanohybrid catalysed reaction, for the first time, was shown to be highly efficient in mild conditions (i.e., room temperature, air) with excellent product yield (92 %) and good recyclability (up to four cycles) at room temperature.

Graphical Abstract


SiO2 nanospheres Graphene oxide (GO) SiO2–GO nanohybrid Functionalized quinoxaline Cyclocondensation reaction 



An Emeritus Scientist Fellowship awarded to MSS by the Council of Scientific and Industrial Research, New Delhi (Project vide NO. 21(0919)/12/EMR-II Dated 25-04-2013) is gratefully acknowledged. The authors are grateful to the UGC for the award of a Teacher fellowship. The authors are also grateful to the Department of Chemistry, Dr. B. A. Marathwada University, Aurangabad, for providing the laboratory facilities. We also thank SAIF Division, CDRI, Lucknow, for providing analytical data.

Supplementary material

11164_2016_2667_MOESM1_ESM.docx (280 kb)
Supplementary material 1 (DOCX 279 kb)


  1. 1.
    L.E. Seitz, W.J. Suling, R.C. Reynolds, J. Med. Chem. 45, 5604 (2002)CrossRefGoogle Scholar
  2. 2.
    C.W. Lindsley, Z. Zhao, W.H. Leister, R.G. Robinson, S.F. Barnett, J.D. Defeo, R.E. Jones, G.D. Hartman, J.R. Huff, H.E. Huber, M.E. Duggan, Bioorg. Med. Chem. Lett. 15, 761 (2005)CrossRefGoogle Scholar
  3. 3.
    M. Loriga, S. Piras, P. Sanna, G. Paglietti, Farmaco 52, 157 (1997)Google Scholar
  4. 4.
    X. Hui, J. Desrivot, C. Bories, P.M. Loisea, X. Franck, R. Hocquemiller, B. Figadere, Bioorg. Med. Chem. Lett. 16, 815 (2006)CrossRefGoogle Scholar
  5. 5.
    Y.B. Kim, Y. Kim, J.Y. Park, S.K. Kim, Bioorg. Med. Chem. Lett. 14, 541 (2004)CrossRefGoogle Scholar
  6. 6.
    R. Rajule, V.C. Bryant, H. Lopez, X. Luo, A. Natarajan, Bioorg. Med. Chem. 20, 2227 (2012)CrossRefGoogle Scholar
  7. 7.
    R. Sarges, H.R. Howard, R.G. Browne, L.A. Lebel, P.A. Seymour, J. Med. Chem. 33, 2240 (1990)CrossRefGoogle Scholar
  8. 8.
    A. Gazit, H. App, G. Mcmahon, J. Chen, A. Levitzki, F.D. Bohmer, J. Med. Chem. 39, 2170 (1996)CrossRefGoogle Scholar
  9. 9.
    E.D. Brock, D.M. Lewis, T.I. Yousaf, H.H. Harper, (The Procter and Gamble Company, USA) WO Patent 9951688 (1999)Google Scholar
  10. 10.
    K.R.J. Thomas, M. Velusamy, J.T. Lin, C.H. Chuen, Y.T. Tao, Chem. Mater. 17, 1860 (2005)CrossRefGoogle Scholar
  11. 11.
    S. Dailey, J.W. Feast, R.J. Peace, R.C. Saga, S. Till, E.L. Wood, J. Mater. Chem. 11, 2238 (2001)CrossRefGoogle Scholar
  12. 12.
    J.L. Sessler, H. Maeda, T. Mizuno, V.M. Lynch, H. Furuta, Am. Chem. Soc. 124, 13474 (2002)CrossRefGoogle Scholar
  13. 13.
    P.P. Castro, G. Zhao, G.A. Masangkay, C. Hernandez, L.M. Gutierrez-Tunstad, Org. Lett. 6, 333 (2004)CrossRefGoogle Scholar
  14. 14.
    V. Narsaiah, J. Kranthi Kumar, Synth. Comm. 42, 883 (2012)CrossRefGoogle Scholar
  15. 15.
    Y. Xu, X. Wan, Tetrahedron Lett. 54, 642 (2013)CrossRefGoogle Scholar
  16. 16.
    S. Antoniotti, E. Dunach, Tetrahedron Lett. 43, 3971 (2002)CrossRefGoogle Scholar
  17. 17.
    F. Pan, T.M. Chen, J.J. Cao, J.P. Zou, W. Zhang, Tetrahedron Lett. 53, 2508 (2012)CrossRefGoogle Scholar
  18. 18.
    L. Nagarapu, R. Mallepalli, G. Arava, L. Yeramanchi, Eur. J. Chem. 1, 228 (2010)CrossRefGoogle Scholar
  19. 19.
    S. Paul, B. Basu, Tetrahedron Lett. 52, 6597 (2011)CrossRefGoogle Scholar
  20. 20.
    P. Ghosh, A. Mandal, Tetrahedron Lett. 53, 6483 (2012)CrossRefGoogle Scholar
  21. 21.
    F.W. Wu, R.S. Hou, H.M. Wang, I.J. Kang, L.C. Chen, Heterocycles 83, 2313 (2011)CrossRefGoogle Scholar
  22. 22.
    T.Q. Huang, Q. Zhang, J.X. Chen, W.X. Gao, J.C. Ding, H. Wu, J. Chem. Res. 761 (2009)Google Scholar
  23. 23.
    R.X. Shi, Y.K. Liu, Z.Y. Xu, J. Zhejiang, Univ. Sci. B 11(2), 102 (2010)CrossRefGoogle Scholar
  24. 24.
    J.P. Wan, S.F. Gan, J.M. Wu, Y.J. Pan, Green Chem. 11, 1633 (2009)CrossRefGoogle Scholar
  25. 25.
    B. Madhav, S.N. Murthy, V.P. Reddy, K.R. Rao, Y.V.D. Nageswar, Tetrahedron Lett. 50, 6025 (2009)CrossRefGoogle Scholar
  26. 26.
    S.B. Wadavrao, R.S. Ghogare, A. Venkat Narsaiah, Org. Commun. 6(1), 23 (2013)Google Scholar
  27. 27.
    B. Das, K. Venkateswarlu, K. Suneel, A. Majhi, Tetrahedron Lett. 48, 5371 (2007)CrossRefGoogle Scholar
  28. 28.
    G. Brahmachari, S. Laskar, P. Barik, RSC Adv. 3, 14245 (2013)CrossRefGoogle Scholar
  29. 29.
    H.K. Kadam, S. Khan, R.A. Kunkalkar, S.G. Tilve, Tetrahedron Lett. 54, 1003 (2013)CrossRefGoogle Scholar
  30. 30.
    B. Roy, S. Ghosh, P. Ghosh, B. Basu, Tetrahedron Lett. 56, 6762 (2015)CrossRefGoogle Scholar
  31. 31.
    R.J. White, R. Luque, V.L. Budarin, J.H. Clark, D.J. MacQuarrie, Chem. Soc. Rev. 38, 481 (2009)CrossRefGoogle Scholar
  32. 32.
    H.M. Yang, X.J. Cui, Y.Q. Deng, F. Shi, Chem. Catal. Chem. 4, 1739 (2013)Google Scholar
  33. 33.
    L. Shang, T. Bian, B. Zhang, D. Zhang, L.-Z. Wu, C.-H. Tung, Y. Yin, T. Zhang, Angew. Chem. Int. Ed. 53, 250 (2014)CrossRefGoogle Scholar
  34. 34.
    S. Wang, Q. Zhao, H. Wei, J.-Q. Wang, M. Cho, H. Sung Cho, O. Terasaki, Y. Wan, J. Am. Chem. Soc. 135, 11849 (2013)CrossRefGoogle Scholar
  35. 35.
    J. Pyun, Angew. Chem. Int. Ed. 50, 46 (2008)CrossRefGoogle Scholar
  36. 36.
    D.R. Dreyer, S. Park, C.W. Bielawski, R.S. Ruoff, Chem. Soc. Rev. 39, 228 (2010)CrossRefGoogle Scholar
  37. 37.
    S. Guo, S. Dong, E. Wang, ACS Nano 4, 547 (2010)CrossRefGoogle Scholar
  38. 38.
    X. Zhou, X. Huang, X. Qi, S. Wu, C. Xue, F.Y.C. Boey, Q. Yan, P. Chen, H. Zhang, J. Phys. Chem. C 113, 10842 (2009)CrossRefGoogle Scholar
  39. 39.
    H.M.A. Hassan, V. Abdelsayed, A.E.R.S. Khder, K.M. AbouZeid, J. Terner, M.S. El-Shall, S.I. Al-Resayes, A.A. El-Azhary, J. Mater. Chem. 19, 3832 (2009)CrossRefGoogle Scholar
  40. 40.
    D. Chen, H.B. Feng, J.H. Li, Chem. Rev. 112, 6027 (2012)CrossRefGoogle Scholar
  41. 41.
    D.R. Dreyer, H.P. Jia, C.W. Bielawski, Angew. Chem. 122, 6965 (2010)CrossRefGoogle Scholar
  42. 42.
    M. Nasrollahzadeh, M. Atarod, B. Jaleh, M. Gandomirouzbahani, Ceram. Int. 42(7), 8587 (2016)CrossRefGoogle Scholar
  43. 43.
    M. Nasrollahzadeh, S.M. Sajadi, A. Rostami-Vartooni, M. Alizadeh, M. Bagherzadeh, J. Colloid Interface Sci. 466, 360 (2016)CrossRefGoogle Scholar
  44. 44.
    M. Atarod, M. Nasrollahzadeh, S. Mohammad Sajadi, J. Colloid Interface Sci. 465, 249 (2016)CrossRefGoogle Scholar
  45. 45.
    M. Atarod, M. Nasrollahzadeh, S. Mohammad, J. Colloid Interface Sci. 465, 249 (2015)CrossRefGoogle Scholar
  46. 46.
    M. Nasrollahzadeh, S. Mohammad Sajadiand, M. Maham, RSC Adv. 5, 40628 (2015)CrossRefGoogle Scholar
  47. 47.
    H.P. Jia, D.R. Dreyer, C.W. Bielawski, Adv. Synth. Catal. 353, 528 (2011)CrossRefGoogle Scholar
  48. 48.
    W. Stober, A. Fink, E. Bohn, J. Collid, Interface Sci. 26, 62 (1968)CrossRefGoogle Scholar
  49. 49.
    B.R. Sathe, X. Zou, T. Asefa, Catalysis science and Technology 4, 2023 (2014)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2016

Authors and Affiliations

  • Praveen V. Shitre
    • 1
  • Rajkumar R. Harale
    • 1
  • Bhaskar R. Sathe
    • 1
  • Murlidhar S. Shingare
    • 1
    Email author
  1. 1.Department of ChemistryDr. Babasaheb Ambedkar Marathwada UniversityAurangabadIndia

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