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SBA-Pr-SO3H: an efficient catalyst for the combinatorial synthesis of functionalized 2-aryl-4-quinazolinones using unusual γ-amino acids

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Abstract

SBA-Pr-SO3H was found as a nanocatalyst for the cyclocondensation of isatoic anhydride, aromatic aldehydes and γ-amino acids (gabapentin and baclofen) to access novel 2-aryl-4-quinazolinone γ-amino acid derivatives in solvent-free reaction conditions in good to high yields. Compared to the classical approaches, this process is a simple, highly yielding, time saving, and environmentally friendly method.

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References

  1. L.F. Tietze (ed.), Domino Reactions (Wiley, Weinheim, 2014)

    Google Scholar 

  2. R.P. Herera, E. Marquez-Lopéz (eds.), Multicomponent Reactions, Concepts and Applications for Design and Synthesis (Wiley, New Jersey, 2015)

    Google Scholar 

  3. R.V. Grieken, J.A. Melero, G. Morales, J. Mol. Catal. A Chem. 256, 29 (2006)

    Article  Google Scholar 

  4. S.L. Burkett, S.D. Sims, S. Mann, Chem. Commun. 1367 (1996)

  5. D.J. Macquarrie, Chem. Commun. 16, 1961 (1996)

    Article  Google Scholar 

  6. X. Feng, G.E. Fryxell, L.Q. Wang, A.Y. Kim, J. Liu, K.M. Kemner, Science 276, 923 (1997)

    Article  CAS  Google Scholar 

  7. W.M. Van Rhijn, D.E. De Vos, B.F. Sels, W.D. Bossaert, P.A. Jacobs, Chem. Commun. 317 (1998)

  8. B. Karimi, D. Zareyee, Org. Lett. 10, 3989 (2008)

    Article  CAS  Google Scholar 

  9. B. Karimi, A. Zamani, Org. Biomol. Chem. 10, 4531 (2012)

    Article  CAS  Google Scholar 

  10. R.I. Kureshy, I. Ahmad, K. Pathak, N.H. Khan, S.H.R. Abdi, R.V. Jasra, Catal. Commun. 10, 572 (2009)

    Article  CAS  Google Scholar 

  11. V. Fathi Vavsari, G. Mohammadi Ziarani, A. Badiei, S. Balalaie, J. Iran. Chem. Soc. 13, 1037 (2016)

    Article  CAS  Google Scholar 

  12. D.J. Connolly, D.O. Cusack, T.P. Sullivan, P.J. Guiry, Tetrahedron 61, 10153 (2005)

    Article  CAS  Google Scholar 

  13. I. Khan, A. Ibrar, W. Ahmed, A. Saeed, Eur. J. Med. Chem. 90, 12 (2015)

    Article  Google Scholar 

  14. J. Bilbro, M. Mart, N. Kyprianou, Anticancer Res. 33, 4695 (2013)

    CAS  Google Scholar 

  15. J. Cai, M. Sun, X. Wu, J. Chen, P. Wang, X. Zong, M. Ji, Eur. J. Med. Chem. 63, 702 (2013)

    Article  CAS  Google Scholar 

  16. A. Baba, N. Kawamura, H. Makino, Y. Ohta, S. Taketomi, T. Sohda, J. Med. Chem. 39, 5176 (1996)

    Article  CAS  Google Scholar 

  17. Y.N. Mabkhot, M.S. Al-Har, D.A. Aldalbahi, Z. Ul-Haq, Molecules 19, 8725 (2014)

    Article  Google Scholar 

  18. V. Alagarsamy, S.V. Raja, K. Dhanabal, Bioorg. Med. Chem. 15, 3457 (2007)

    Article  CAS  Google Scholar 

  19. V. Alagarsamy, V.R. Solomon, K. Dhanapala, Bioorg. Med. Chem. 15, 235 (2007)

    Article  CAS  Google Scholar 

  20. V. Jatav, S. Kashaw, P. Mishra, Med. Chem. Res. 17, 205 (2008)

    Article  Google Scholar 

  21. M.S. Malamas, J. Millen, J. Med. Chem. 34, 1492 (1991)

    Article  CAS  Google Scholar 

  22. ShN Khattab, N.S. Haiba, A.M. Asal, A.A. Bekhit, A. Amer, H.L. Abdel-Rahman, A. El-Faham, Bioorg. Med. Chem. 23, 3574 (2015)

    Article  CAS  Google Scholar 

  23. M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgary, A.A. Mohammadi, Tetrahedron Lett. 46, 6123 (2005)

    Article  CAS  Google Scholar 

  24. S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, H. Sepehrian, S. Ebrahimi, Synthesis 1356 (2010)

  25. L.M. Wang, I. Hu, J.H. Shao, J.J. Yu, L. Zhang, J. Flourine Chem. 129, 1139 (2008)

    Article  CAS  Google Scholar 

  26. H.R. Shaterian, A.R. Oveisi, Chin. J. Chem. 27, 2418 (2009)

    Article  CAS  Google Scholar 

  27. C. Jiuxi, W. Dengze, H. Fei, L. Miaochang, W. Huayue, D. Jinchang, S. Weike, Tetrahedron Lett. 49, 3814 (2008)

    Article  Google Scholar 

  28. K. Ramesh, K. Karnakar, G. Satish, K.V.R. Harsha, Y.V.D. Nageswar, Tetrahedron Lett. 53, 6095 (2012)

    Article  CAS  Google Scholar 

  29. Y. Chen, W. Shan, M. Lei, L. Hu, Tetrahedron Lett. 53, 5923 (2012)

    Article  CAS  Google Scholar 

  30. M. Prakash, V. Kesavan, Org. Lett. 14, 1896 (2012)

    Article  CAS  Google Scholar 

  31. M. Wang, T.T. Zhang, Y. Liang, J.J. Gao, Monatsh. Chem. 143, 835 (2012)

    Article  CAS  Google Scholar 

  32. A. Saffar-Teluri, S. Bolouk, Monatsh. Chem. 141, 1113 (2010)

    Article  CAS  Google Scholar 

  33. W. Shu-Liang, Y. Ke, W. Xiang-Shan, Chin. J. Org. Chem. 31, 1235 (2011)

    Google Scholar 

  34. G. Wheeler, Curr. Opin. Investig. Drugs 3, 470 (2002)

    CAS  Google Scholar 

  35. H. Stefan, T.J. Feuerstein, Pharmacol. Ther. 113, 165 (2007)

    Article  CAS  Google Scholar 

  36. P.G. Vasudev, S. Chatterjee, N. Shamala, P. Balaram, Acc. Chem. Res. 42, 1628 (2009)

    Article  CAS  Google Scholar 

  37. A. Salimbeni, F. Paleari, R. Canevotti, M. Criscuoli, A. Lippi, M. Angiolini, L. Belvisi, C. Scolastico, L. Colombo, Bioorg. Med. Chem. Lett. 7, 2205 (1997)

    Article  CAS  Google Scholar 

  38. M. Tajbakhsh, S. Ramezanpour, S. Balalaie, H.R. Bijanzadeh, J. Heterocycl. Chem. 52, 1559 (2015)

    Article  CAS  Google Scholar 

  39. E. Ghabraie, S. Mehrparvar, S. Balalaie, F. Rominger, J. Org. Chem. 79, 7926 (2014)

    Article  CAS  Google Scholar 

  40. E. Ghabraie, S. Balalaie, Helv. Chim. Acta 97, 1555 (2014)

    Article  CAS  Google Scholar 

  41. H.R. Bijanzadeh, S. Mehrparvar, S. Balalaie, J. Iran. Chem. Soc. 10, 1859 (2015)

    Article  Google Scholar 

  42. S. Balalaie, M. Kassaee, H.R. Bijanzadeh, F. Darvish, M. Bararjanian, F. Jalaiyan, J. Iran. Chem. Soc. 111, 1483 (2014)

    Article  Google Scholar 

  43. V. Fathi Vavsari, V. Dianati, S. Ramezanpour, S. Balalaie, Synlett 26, 14 (2015)

    Google Scholar 

  44. V. Fathi Vavsari, G. Mohammadi Ziarani, S. Balalaie, A. Latifi, M. Karimi, A. Badiei, Tetrahedron 72, 35 (2016)

    Google Scholar 

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Acknowledgment

Saeed Balalaie gratefully acknowledges Iran National Science Foundation (INSF) for financial support.

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Authors and Affiliations

  1. Department of Chemistry, North Branch of Tehran, Islamic Azad University, Tehran, Iran

    Shohreh Hekmat & Hasan Kabiri-Fard

  2. Peptide Chemistry Research Center, K. N. Toosi University of Technology, P. O. Box 15875-4416, Tehran, Iran

    Saeed Balalaie, Sorour Ramezanpour & Vaezeh Fathi Vavsari

  3. Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran

    Saeed Balalaie

  4. Organisch-Chemisches Institut der Universitaet Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany

    Frank Rominger

Authors
  1. Shohreh Hekmat
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  2. Saeed Balalaie
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  3. Sorour Ramezanpour
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  4. Frank Rominger
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  5. Vaezeh Fathi Vavsari
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  6. Hasan Kabiri-Fard
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Correspondence to Saeed Balalaie.

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Hekmat, S., Balalaie, S., Ramezanpour, S. et al. SBA-Pr-SO3H: an efficient catalyst for the combinatorial synthesis of functionalized 2-aryl-4-quinazolinones using unusual γ-amino acids. J IRAN CHEM SOC 14, 833–841 (2017). https://doi.org/10.1007/s13738-016-1033-5

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