Advertisement

Research on Chemical Intermediates

, Volume 41, Issue 6, pp 3719–3727 | Cite as

Cellulose@Fe2O3 nanoparticle composites: magnetically recyclable nanocatalyst for the synthesis of 3-aminoimidazo[1,2-a]pyridines

  • Ahmad ShaabaniEmail author
  • Hamed Nosrati
  • Mozhdeh Seyyedhamzeh
Article

Abstract

3-Aminoimidazo[1,2-a]pyridines have been synthesized through a condensation reaction of 2-aminopyridine, an aldehyde and an alkyl or aryl isocyanide in high yields in the presence of a catalytic amount of cellulose@Fe2O3 as a magnetically recoverable heterogeneous catalyst. High catalytic activity, good reusability, and simple magnetic work-up are some of the salient features of the present protocol.

Graphical Abstract

Keywords

Cellulose@Fe2O3 Magnetic Nanoparticle 3-Aminoimidazo[1,2-a]pyridines Isocyanide 

Notes

Acknowledgments

We gratefully acknowledge financial support from the Iran National Elites Foundation (INEF) and the Research Council of Shahid Beheshti University.

References

  1. 1.
    A. Gueiffier, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, M. Witvrouw, J. Balzarini, J. Med. Chem. 41, 5108 (1998)Google Scholar
  2. 2.
    T. Kercher, C. Rao, J.R. Bencsik, J.A. Josey, J. Comb. Chem. 9, 1177 (2007)Google Scholar
  3. 3.
    J.E. Starrett Jr, T.A. Montzka, A.R. Crosswell, R.L. Cavanagh, J. Med. Chem. 32, 2204 (1989)Google Scholar
  4. 4.
    A.M. Palmer, S. Chrismann, G. Münch, C. Brehm, P.J. Zimmermann, W. Buhr, J. Senn-Bilfinger, M.P. Feth, W.A. Simon, Bioorg. Med. Chem. 17, 368 (2009)Google Scholar
  5. 5.
    T. Michiaki, Y. Yung-Hsiung, N. Kazuyuki, O. Hidenori, EP0052016 (1982)Google Scholar
  6. 6.
    C. Maul, B. Sundermann, H.H. Hennie, J. Schneider, M. Gerlach, WO01027109 (2001)Google Scholar
  7. 7.
    J.-B. Véron, H. Allouchi, C. Enguehard-Gueiffier, R. Snoeck, G. Andrei, E. De Clercq, A. Gueiffier, Bioorg. Med. Chem. 16, 9536 (2008)Google Scholar
  8. 8.
    K.S. Gudmundsson, B.A. Johns, Bioorg. Med. Chem. Lett. 17, 2735 (2007)Google Scholar
  9. 9.
    C. Enguehard-Gueiffier, A. Gueiffier, Mini-Rev. Med. Chem. 7, 888 (2007)Google Scholar
  10. 10.
    H. Bienayme, K. Bouzid, Angew. Chem. Int. Ed. 37, 2234 (1998)Google Scholar
  11. 11.
    K. Groebke, L. Weber, F. Mehlin, Synlett 6, 661 (1998)CrossRefGoogle Scholar
  12. 12.
    C. Blackburn, Tetrahedron Lett. 39, 5469 (1998)Google Scholar
  13. 13.
    C. Blackburn, B. Guan, P. Fleming, K. Shiosaki, S. Tsai, Tetrahedron Lett. 39, 3635 (1998)Google Scholar
  14. 14.
    C. Blackburn, B. Guan, Tetrahedron Lett. 41, 1495 (2000)Google Scholar
  15. 15.
    S.M. Ireland, H. Tye, M. Whittaker, Tetrahedron Lett. 44, 4369 (2003)Google Scholar
  16. 16.
    A.L. Rousseau, P. Matlaba, C.J. Parkinson, Tetrahedron Lett. 48, 4079 (2007)Google Scholar
  17. 17.
    A. Shaabani, E. Soleimani, A. Sarvary, A.H. Rezayan, A. Maleki, Chin. J. Chem. 27, 369 (2009)Google Scholar
  18. 18.
    S.K. Guchhait, C. Madaan, B.S. Thakkar, Synthesis 19, 3293 (2009)CrossRefGoogle Scholar
  19. 19.
    E.F. Dimauro, J.M. Kennedy, J. Org. Chem. 72, 1013 (2007)Google Scholar
  20. 20.
    A.T. Khan, R. Sidick Basha, M. Lal, Tetrahedron Lett. 53, 2211 (2012)Google Scholar
  21. 21.
    A. Shaabani, E. Soleimani, A. Maleki, Monatsh. Chem. 138, 73 (2006)Google Scholar
  22. 22.
    A. Shaabani, A. Maleki, J. Moghimi Rad, E. Soleimani, Chem. Pharm. Bull. 55, 957 (2007)Google Scholar
  23. 23.
    A. Shaabani, M. Seyyedhamzeh, S. Shaabani, N. Ganji, Res. Chem. Intermed. (2013). doi: 10.1007/s11164-013-1352-4 Google Scholar
  24. 24.
    S. Shylesh, V. Schünemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 3428 (2010)Google Scholar
  25. 25.
    S. Abbet, U. Heiz, in Nanocatalysis, ed. by C.N.R. Rao, A.A. Muller, K. Cheetham (Wiley-VCH, Weinheim, 2004), p. 555Google Scholar
  26. 26.
    V. Rajpara, S. Banerjee, G. Sereda, Synthesis 16, 2835 (2010)CrossRefGoogle Scholar
  27. 27.
    G. Gao, H. Wu, Y. Zhang, K. Wang, P. Huang, X. Zhang, S. Guo, D. Cui, J. Mater. Chem. 21, 12224 (2011)Google Scholar
  28. 28.
    S. Gai, P. Yang, D. Wang, C. Li, X. Li, N. Niu, J. Lin, J. Mater. Chem. 21, 16420 (2011)Google Scholar
  29. 29.
    I.F. Nata, M. Sureshkumar, C.-K. Lee, Rsc Adv. 1, 625 (2011)Google Scholar
  30. 30.
    E. Guibal, Prog. Polym. Sci. 30, 71 (2005)Google Scholar
  31. 31.
    D. Klemm, B. Heublein, H.P. Fink, A. Bohn, Angew. Chem. Int. Ed. 44, 3358 (2005)Google Scholar
  32. 32.
    Y. Habibi, L.A. Lucia, O.J. Rojas, Chem. Rev. 110, 3479 (2010)Google Scholar
  33. 33.
    C. Johansson, J. Bras, I. Mondragon, P. Nechita, D. Plackett, P. Simon, D.G. Svetec, S. Virtanen, M.G. Baschetti, C. Breen, Bioresources 7, 2506 (2012)CrossRefGoogle Scholar
  34. 34.
    M. Gericke, J. Trygg, P. Fardim, Chem. Rev. 113, 4812 (2013)Google Scholar
  35. 35.
    X. Yu, S. Tong, M. Ge, J. Zuo, C. Cao, W. Song, J. Mater. Chem. A 1, 959 (2013)Google Scholar
  36. 36.
    A. Shaabani, A. Maleki, Appl. Catal. A 331, 149 (2007)Google Scholar
  37. 37.
    A. Shaabani, A. Rahmati, Z. Badri, Catal. Commun. 9, 13 (2008)Google Scholar
  38. 38.
    A. Shaabani, M. Seyyedhamzeh, A. Maleki, F. Rezazadeh, Appl. Catal. A 358, 146 (2009)Google Scholar
  39. 39.
    H. Mofakham, Z. Hezarkhani, A. Shaabani, J. Mol. Catal. A 360, 26 (2012)Google Scholar
  40. 40.
    A. Shaabani, A. Maleki, Monatsh. Chem. 138, 51 (2006)Google Scholar
  41. 41.
    A. Shaabani, E. Soleimani, A. Maleki, Tetrahedron Lett. 47, 3031 (2006)Google Scholar
  42. 42.
    A. Shaabani, E. Soleimani, A. Maleki, J. Moghimi-Rad, Synth. Commun. 38, 1090 (2008)Google Scholar
  43. 43.
    N. Anand, K.H.P. Reddy, T. Satyanarayana, K.S.R. Rao, D.R. Burri, Catal. Sci. Technol. 2, 570 (2012)Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Ahmad Shaabani
    • 1
    Email author
  • Hamed Nosrati
    • 1
  • Mozhdeh Seyyedhamzeh
    • 1
  1. 1.Faculty of ChemistryShahid Beheshti University, G.C.TehranIran

Personalised recommendations