Synthesis of 3,4,5-substituted furan-2(5H)-ones using Al-doped ZnO nanostructure

  • Majid Ghashang
  • Sadaf Janghorban
  • Seyyed Jalal Roudbaraki
Article
  • 4 Downloads

Abstract

Al-doped ZnO nanostructures were prepared via a simple precipitation method and were characterized by several techniques including XRD, TEM, EDX, UV–Vis, and DLS. All XRD patterns show the hexagonal single-phase structure of pure and Al-doped ZnO nanopowders without impurity. The samples consist of particles with average sizes ranging from 53 to 60 nm measured by DLS technique. Next, the catalytic activity of pure and Al-doped ZnO nanopowders was investigated in terms of synthesis of 3,4,5-substituted furan-2(5H)-one derivatives using the three-component reaction of aldehydes, aromatic amines, and acetylenic esters. This procedure has advantages such as high yields, simple methodology, and easy work-up.

Keywords

3,4,5-substituted furan-2(5H)-one Al-doped ZnO ZnO Acetylenic esters Butenolides 

Notes

Acknowledgements

We are thankful to the Najafabad Branch of the Islamic Azad University Research Council for partial support of this research.

References

  1. 1.
    B. Clark, R.J. Capon, E. Lacey, S. Tennant, J.H. Gill, B. Bulheller, G. Bringmann, J. Nat. Prod. 68, 1226 (2005)CrossRefGoogle Scholar
  2. 2.
    M.M. Baag, N.P. Argade, Synthesis 2008, 26 (2008)CrossRefGoogle Scholar
  3. 3.
    S.-C. Lee, G.D. Brown, J. Nat. Prod. 61, 29 (1998)CrossRefGoogle Scholar
  4. 4.
    M. Seitz, O. Reiser, Curr. Opin. Chem. Biol. 9, 285 (2005)CrossRefGoogle Scholar
  5. 5.
    T.M. Ugurchieva, V.V. Veselovsky, Russ. Chem. Rev. 78, 337 (2009)CrossRefGoogle Scholar
  6. 6.
    Y.S. Rao, Chem. Rev. 76, 625 (1976)CrossRefGoogle Scholar
  7. 7.
    X. Jusseau, L. Chabaud, C. Guillou, Tetrahedron 70, 2595 (2014)CrossRefGoogle Scholar
  8. 8.
    R. Rossi, F. Bellina, M. Biagetti, L. Mannina, Tetrahedron Lett. 39, 7799 (1998)CrossRefGoogle Scholar
  9. 9.
    L.M. Levy, G.M. Cabrera, J.E. Wright, A.M. Seldes, Phytochemistry 62, 239 (2003)CrossRefGoogle Scholar
  10. 10.
    S.M. Hein, J.B. Gloer, B. Koster, D. Malloch, J. Nat. Prod. 64, 809 (2001)CrossRefGoogle Scholar
  11. 11.
    M. Pour, M. Spulak, V. Balsanek, J. Kunes, P. Kubanova, V. Butcha, Bioorg. Med. Chem. 11, 2843 (2003)CrossRefGoogle Scholar
  12. 12.
    S. Padakanti, M. Pal, K.R. Yeleswarapu, Tetrahedron 59, 7915 (2003)CrossRefGoogle Scholar
  13. 13.
    T.R. Hoye, L. Tan, Tetrahedron Lett. 36, 1981 (1995)CrossRefGoogle Scholar
  14. 14.
    S. Takahashi, A. Kubota, T. Nakata, Tetrahedron Lett. 43, 8661 (2002)CrossRefGoogle Scholar
  15. 15.
    S. Hanessian, R.Y. Park, R.Y. Yang, Synlett 1997, 351 (1997)CrossRefGoogle Scholar
  16. 16.
    A. Choudhury, F. Jin, D. Wang, Z. Wang, G. Xu, D. Nguyen, J. Castoro, M.E. Pierce, P.N. Confalone, Tetrahedron Lett. 44, 247 (2003)CrossRefGoogle Scholar
  17. 17.
    B. Beck, M. Magnin-Lachaux, E. Herdtweck, A. Dömling, Org. Lett. 3, 2875 (2001)CrossRefGoogle Scholar
  18. 18.
    E. Genin, P.Y. Toullec, S. Antoniotti, C. Brancour, J.-P. Genêt, V. Michelet, J. Am. Chem. Soc. 128, 3112 (2006)CrossRefGoogle Scholar
  19. 19.
    Q. Zhang, M. Cheng, X. Hu, B.-G. Li, J.-X. Ji, J. Am. Chem. Soc. 132, 7256 (2010)CrossRefGoogle Scholar
  20. 20.
    S. Ma, Z. Shi, J. Org. Chem. 63, 6387 (1998)CrossRefGoogle Scholar
  21. 21.
    Y. Wu, W. Yao, L. Pan, Y. Zhang, C. Ma, Org. Lett. 12, 640 (2010)CrossRefGoogle Scholar
  22. 22.
    Y.-Q. Zhu, T.-F. Han, J.-L. He, M. Li, J.-X. Li, K. Zhu, J. Org. Chem. 82, 8598 (2017)CrossRefGoogle Scholar
  23. 23.
    B.R. Park, K.H. Kim, J.W. Lim, J.N. Kim, Tetrahedron Lett. 53, 36 (2012)CrossRefGoogle Scholar
  24. 24.
    S.N. Murthy, B. Madhav, A. Vijay Kumar, K. Rama Rao, Y.V.D. Nageswar, Tetrahedron 65, 5251 (2009)CrossRefGoogle Scholar
  25. 25.
    L. Nagarapu, U.N. Kumar, P. Upendra, R. Bantu, Synth. Commun. 42, 2139 (2012)CrossRefGoogle Scholar
  26. 26.
    S.U. Tekale, S.S. Kauthale, V.P. Pagore, V.B. Jadhav, R.P. Pawar, J. Iran. Chem. Soc. 10, 1271 (2013)CrossRefGoogle Scholar
  27. 27.
    M.R. Mohammad Shafiee, M. Kargar Biointerface, Res. Appl. Chem. 7, 2170 (2017)Google Scholar
  28. 28.
    M.R. Mohammad Shafiee, S.S. Mansoor, M. Ghashang, A. Fazlinia, Compt. Rend. Chim. 17, 131 (2014)CrossRefGoogle Scholar
  29. 29.
    R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, Chin. Chem. Lett. 24, 901 (2013)CrossRefGoogle Scholar
  30. 30.
    R. Doostmohammadi, N. Hazeri, Lett. Org. Chem. 10, 199 (2013)CrossRefGoogle Scholar
  31. 31.
    J. Safaei-Ghomi, E. Heidari-Baghbahadorani, H. Shahbazi-Alavi, Monatsh. Chem. 146, 181 (2015)CrossRefGoogle Scholar
  32. 32.
    F. Bahramian, A. Fazlinia, S.S. Mansoor, M. Ghashang, F. Azimi, M.N. Biregan, Res. Chem. Intermed. 42, 6501 (2016)CrossRefGoogle Scholar
  33. 33.
    M. Ghashang, Curr. Org. Synth. 9, 727 (2012)CrossRefGoogle Scholar
  34. 34.
    M. Ghashang, S.S. Mansoor, K. Aswin, Chin. J. Catal. 35, 127 (2014)CrossRefGoogle Scholar
  35. 35.
    H. Taghrir, M. Ghashang, M. Najafi Biregan, Chin. Chem. Lett. 27, 119 (2016)CrossRefGoogle Scholar
  36. 36.
    M. Ghashang, Res. Chem. Intermed. 42, 4191 (2016)CrossRefGoogle Scholar
  37. 37.
    M. Ghashang, M. Kargar, M.R.M. Shafiee, S.S. Mansoor, A. Fazlinia, H. Esfandiari, Recent Pat. Nanotechnol. 9, 204 (2015)CrossRefGoogle Scholar
  38. 38.
    M. Ghashang, S.S. Mansoor, M.R. Mohammad Shafiee, M. Kargar, M. Najafi Biregan, F. Azimi, H. Taghrir, J. Sulfur Chem. 37, 377 (2016)CrossRefGoogle Scholar
  39. 39.
    A. Baziar, M. Ghashang, React. Kinet. Mech. Catal. 118, 463 (2016)CrossRefGoogle Scholar
  40. 40.
    M. Ghashang, S.S. Mansoor, L. Shams Solaree, A. Sharifian-esfahani, Iran. J. Catal. 6, 237 (2016)Google Scholar
  41. 41.
    M.R. Mohammad Shafiee, M. Kargar, M.S. Hashemi, M. Ghashang, Curr. Nanosci. 12, 645 (2016)CrossRefGoogle Scholar
  42. 42.
    M. Ghashang, Biointerface Res. Appl. Chem. 6, 1338 (2016)Google Scholar
  43. 43.
    N. Sheikhan-Shamsabadi, M. Ghashang, Main Group Met. Chem. 40, 19 (2016)Google Scholar
  44. 44.
    M.R. Mohammad Shafiee, A. Sattari, M. Kargar, M. Ghashang, Steel Compos. Struct. 24, 15 (2016)CrossRefGoogle Scholar
  45. 45.
    M.M. Hassan, W. Khan, A. Azam, A.H. Naqvi, J. Lumin. 145, 160 (2014)CrossRefGoogle Scholar
  46. 46.
    M.A.M. Khan, S. Kumar, M.N. Khan, M. Ahamed, A.S. Al Dwayyan, J. Lumin. 155, 275 (2014)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of Sciences, Najafabad BranchIslamic Azad UniversityNajafabadIran
  2. 2.Department of Chemistry, Faculty of Sciences, Lahijan BranchIslamic Azad UniversityLahijanIran

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