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Use of nano-CuY zeolite as an efficient and eco-friendly nanocatalyst for facile synthesis of perimidine derivatives

Research on Chemical Intermediates volume 41, pages 3235–3242 (2015)Cite this article

Abstract

A simple and practical procedure is described for synthesis of 2-aryl dihydroperimidines. One-pot reaction of 1,8-diaminonaphthalene with a variety of aromatic aldehydes, in the presence of nano-copper Y zeolite as highly efficient catalyst, was performed in ethanol at room temperature. The CuY zeolite nanocatalyst was characterized by scanning electron microscopy (SEM). Novel compounds were characterized by spectroscopic and spectrometric analyses. This environmentally benign and clean synthetic procedure has several advantages, including the availability, safety, and reusability of the catalyst, high yields, short reaction times, and easy and rapid isolation of the product.

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Fig. 1
Scheme 1

References

  1. K. Undheim, C. Benneche, in Comprehensive Heterocyclic Chemistry II, ed. by A.R. Katritzky, C.W. Rees, E.F. Scriven (Pergamon, Oxford, 1996)

    Google Scholar 

  2. A.F. Pozharskii, V.V. Dalnikovskaya, Russ. Chem. Rev. 50, 816 (1981)

    Article  Google Scholar 

  3. X. Bu, L.W. Deady, G.J. Finlay, B.C. Baguley, W.A. Denny, J. Med. Chem. 44, 2004 (2001)

    Article  CAS  Google Scholar 

  4. J.M. Herbert, P.D. Woodgate, W.A. Denny, J. Med. Chem. 30, 2081 (1987)

    Article  CAS  Google Scholar 

  5. D.P. Panchasara, S. Pande, E-J. Chem. 6, 591 (2009)

    Article  Google Scholar 

  6. D.R. Luthin, A.K. Rabinovich, D.R. Bhumralkar, K.L. Youngblood, R.A. Bychowski, D.S. Dhanoa, J.M. May, Bioorg. Med. Chem. Lett. 9, 765 (1999)

    Article  CAS  Google Scholar 

  7. F.A. Bassyouni, S.M. Abu-Bakr, K.H. Hegab, W. El-Eraky, A.A. El Beih, M.E. Abdel Rehim, Res. Chem. Intermed. 38, 1527 (2012)

    Article  CAS  Google Scholar 

  8. V. Paragamian, M.B. Baker, B.M. Puma, J. Reale, J. Heterocycl. Chem. 5, 591 (1968)

    Article  CAS  Google Scholar 

  9. A. Shaabani, A. Maleki, Chem. Pharm. Bull. 56, 79 (2008)

    Article  CAS  Google Scholar 

  10. J.B. Hendrickson, M.S. Hussoin, J. Org. Chem. 52, 4137 (1987)

    Article  Google Scholar 

  11. J.J. Vanden Eynde, F. Delfosse, A. Mayence, Y.V. Haverbeke, Tetrahedron 51, 5813 (1995)

    Article  CAS  Google Scholar 

  12. I. Yavari, H. Mostafavi, D. Tahmassebi, R. Hekmat-Shoar, Monatsh, Chem. 128, 675 (1997)

    CAS  Google Scholar 

  13. V.A. Ozeryanskii, E.A. Filatova, V.I. Sorokin, A.F. Pozharskii, Russ. Chem. Bull. 50, 846 (2001)

    Article  CAS  Google Scholar 

  14. A. Maquestiau, L. Berte, A. Mayence, L. Vanden Eynd, Synth. Commun. 21, 2171 (1991)

    Article  CAS  Google Scholar 

  15. A. Mobinikhaledi, P.J. Steel, Synth. React. Inorg. Met.-Org. Chem. 39, 2009 (133)

    Google Scholar 

  16. S.-L. Zhang, J.-M. Zhang, Chin. J. Chem. 26, 185 (2008)

    Article  CAS  Google Scholar 

  17. J. Zhang, S. Zhang, Synth. Commun. 37, 2615 (2007)

    Article  CAS  Google Scholar 

  18. M.M. Belmonte, E.C. Escudero-Adán, J. Benet-Buchholz, R.M. Haak, A.W. Kleij, Eur. J. Org. Chem. 2010, 4823 (2010)

    Article  Google Scholar 

  19. A. Mobinikhaledi, H. Moghanian, F. Sasani, Int.J. Green Nanotechnol Phys. Chem. 2, 47 (2010)

    Article  Google Scholar 

  20. O. Maloshitskaya, J. Sinkkonen, V.V. Ovcharenko, K.N. Zelenin, K. Pihlaj, Tetrahedron 60, 6913 (2004)

    Article  CAS  Google Scholar 

  21. L.W. Deady, T. Rodemann, J. Heterocycl. Chem. 35, 1417 (1998)

    Article  CAS  Google Scholar 

  22. N. Morita, J.I. Dickstein, S.I. Miller, J. Chem. Soc. Perkin Trans. 1, 2103 (1979)

    Article  Google Scholar 

  23. I. Yavari, F. Jahanimoghaddam, F. Adib, H.R. Bijanzadeh, Tetrahedron 58, 6901 (2002)

    Article  CAS  Google Scholar 

  24. I.A.S. Smellie, A. Fromm, R.M. Paton, Tetrahedron Lett. 50, 4104 (2009)

    Article  CAS  Google Scholar 

  25. A. Mobinikhaledi, N. Foroughifar, N. Basaki, Turk. J. Chem. 33, 555 (2009)

    CAS  Google Scholar 

  26. M. Tajbakhsh, M.M. Heravi, B. Mohajerani, A. Ahmadi, J. Mol. Catal. A 247, 213 (2006)

    Article  CAS  Google Scholar 

  27. R.A. Sheldon, R.S. Downing, Appl. Catal. A 189, 163 (1999)

    Article  CAS  Google Scholar 

  28. L. Bournay, D. Casanave, B. Delfort, G. Hillion, J.A. Chodorge, Catal. Today 106, 190 (2005)

    Article  CAS  Google Scholar 

  29. Y.X. Yang, R.K. Singh, P.A. Webley, Adsorption 14, 265 (2008)

    Article  CAS  Google Scholar 

  30. G. Centi, L. dall’Olio, S. Perathoner, P. Generali, Ind. Eng. Chem. Res. 39, 131 (2000)

    Article  CAS  Google Scholar 

  31. M. Salavati-Niasari, Trans. Met. Chem. 32, 1 (2007)

    Article  CAS  Google Scholar 

  32. S. Vijaikumar, T. Subramanian, K. Pitchumani, J. Nanomater. 49, 1818 (2008)

    Google Scholar 

  33. X.-J. Tang, J.-H. Fei, Z.-Y. Hou, X.-M. Zheng, H. Lou, Energy Fuels 22, 2877 (2008)

    Article  CAS  Google Scholar 

  34. M. Zendehdel, H. Khanmohamadi, M. Mokhtari, J. Chin. Chem. Soc. 57, 205 (2010)

    Article  CAS  Google Scholar 

  35. A. Mobinikhaledi, N. Foroughifar, M.A. Bodaghi-Fard, H. Moghanian, S. Ebrahimi, M. Kalhor, Synth. Commun. 39, 1166 (2009)

    Article  CAS  Google Scholar 

  36. M. Kalhor, A. Mobinikhaledi, J. Jamshidi Res, Chem. Intermed. 39, 3127 (2013)

    Article  CAS  Google Scholar 

  37. M. Kalhor, N. Khodaparast, M. Zendehdel, Lett. Org. Chem. 10, 573 (2013)

    Article  CAS  Google Scholar 

  38. D.W. Breck, N.Y. Tonawanda, Assigned to Union Corbide pat. No 3130007 (1964)

  39. M. Zendehdel, A. Mobinikhaledi, J.F. Hasanvand, J. Incl. Phenom. Macrocycl. Chem. 59, 41 (2007)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, 19395-4697, Tehran, Islamic Republic of Iran

    Mehdi Kalhor & Nooshin Khodaparast

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  1. Mehdi Kalhor
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  2. Nooshin Khodaparast
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Correspondence to Mehdi Kalhor.

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Kalhor, M., Khodaparast, N. Use of nano-CuY zeolite as an efficient and eco-friendly nanocatalyst for facile synthesis of perimidine derivatives. Res Chem Intermed 41, 3235–3242 (2015). https://doi.org/10.1007/s11164-013-1428-1

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  • DOI: https://doi.org/10.1007/s11164-013-1428-1

Keywords

  • Perimidine
  • Catalyst
  • Arylaldehyde
  • Transition nano-metal zeolite