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A convenient synthesis of novel 5-arylidene-2-imino-4-thiazolidinones using base supported ionic liquid-like phase (SILLP) as efficient green catalyst

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Abstract

A facile and convenient protocol was developed for the synthesis of 5-arylidene-2-imino-4-thiazolidinones using solid basic catalyst immobilized onto supported ionic liquid-like phase (SILLP) in high yields (80–95%). The X-ray analysis of the representative compound established the Z configuration of the product at the chiral axis.

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References

  1. A. Verma, S.K. Saraf, Eur. J. Med. Chem. 43, 897 (2008)

    Article  CAS  Google Scholar 

  2. S. Singh, S.S. Parmar, K. Raman, V.I. Stenberg, Chem. Rev. 81, 175 (1981)

    Article  CAS  Google Scholar 

  3. Z. Liu, Y. Huang, W. Zhang, L. Ma, J. Li, X. Wang, J. Li, J. Shen, J. Comb. Chem. 10, 632 (2008)

    Article  CAS  Google Scholar 

  4. R. Ottanà, R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Sautebin, S. Cuzzocread, M.G. Vigorita, Bioorg. Med. Chem. 13, 4243 (2005)

    Article  Google Scholar 

  5. R. Ottanà, R. Maccari, R. Ciurleo, P. Paoli, M. Jacomelli, G. Manao, G. Camici, C. Laggner, T. Langer, Bioorg. Med. Chem. 17, 1928 (2009)

    Article  Google Scholar 

  6. T. Kato, T. Ozaki, K. Tamura, Y. Suzuki, M. Akima, N. Ohi, J. Med. Chem. 41, 4309 (1998)

    Article  CAS  Google Scholar 

  7. T. Kato, T. Ozaki, K. Tamura, Y. Suzuki, M. Akima, N. Ohi, J. Med. Chem. 42, 3134 (1999)

    Article  CAS  Google Scholar 

  8. M.V. Diurno, O. Mazzoni, E. Piscopo, A. Calignano, F. Giordano, A. Bolognesell, J. Med. Chem. 35, 2910 (1992)

    Article  CAS  Google Scholar 

  9. A. Geronikaki, P. Eleftheriou, P. Vicini, I. Alam, A. Dixit, A.K. Saxena, J. Med. Chem. 51, 5221 (2008)

    Article  CAS  Google Scholar 

  10. P. Vicini, A. Geronikaki, K. Anastasia, M. Incerti, F. Zani, Bioorg. Med. Chem. 14, 3859 (2006)

    Article  CAS  Google Scholar 

  11. R. Ottanà, S. Carotti, R. Maccari, I. Landini, G. Chiricosta, B. Caciagli, M.G. Vigorita, E. Mini, Bioorg. Med. Chem. Lett. 15, 3930 (2005)

    Article  Google Scholar 

  12. R. Ottanà, R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Sautebin, S. Cuzzocrea, M.G. Vigorita, Bioorg. Med. Chem. 13, 4243 (2005)

    Article  Google Scholar 

  13. P.C. Lv, C.F. Zhou, J. Chen, P.G. Liu, K.R. Wang, W.J. Mao, H.Q. Li, Y. Yang, J. Xiong, H.L. Zhu, Bioorg. Med. Chem. Lett. 19, 2819 (2009)

    Article  Google Scholar 

  14. R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouque, E.D. Clercq, Bioorg. Med. Chem. 15, 1725 (2007)

    Article  CAS  Google Scholar 

  15. K.S. Ahmad, M. Yusuf, Eur. J. Med. Chem. 44, 2597 (2009)

    Article  Google Scholar 

  16. X. Zhang, X. Li, D. Li, G. Qu, J. Wang, P.M. Loiseau, X. Fan, Bioorg. Med. Chem. Lett. 15, 6280 (2009)

    Article  Google Scholar 

  17. T. Kline, K.C. Barry, S.R. Jackson, H.B. Felise, H.V. Nguyen, S.I. Miller, Bioorg. Med. Chem. Lett. 19, 1340 (2009)

    Article  CAS  Google Scholar 

  18. M.C. Munson, A.W. Cook, J.A. Josey, C. Rao, Tetrahedron Lett. 39, 7223 (1998)

    Article  CAS  Google Scholar 

  19. C.T. Sadashiva, J.N. Narendra Sharath Chandra, C.V. Kavitha, A. Thimmegowda, M.N. Subhash, K.S. Rangappa, Eur. J. Med. Chem. 44, 4848 (2009)

    Google Scholar 

  20. M.H. Shih, F. Ying Ke, Bioorg. Med. Chem. 12, 4633 (2004)

    Article  CAS  Google Scholar 

  21. H. Zhou, Z. Wu, S. Zhai, A. Liu, A. Sun, R. Li, Y. Zhang, S. Ekins, P.W. Swaan, B. Fang, B. Zhang, B. Yan, J. Med. Chem. 51, 242 (2008)

    Google Scholar 

  22. B.L. Barreca, J. Balzarini, A. Chimirri, E.D. Clercq, L.D. Luca, H.D. Höltje, M. Höltje, A.M. Monforte, P. Monforte, C. Pannecouque, A. Rao, M. Zappalà, J. Med. Chem. 45, 5410 (2002)

    Article  CAS  Google Scholar 

  23. J.A. Linthorst, Found. Chem. 12, 55 (2010)

    Article  CAS  Google Scholar 

  24. M.T. Garcia, N. Gathergood, P.J. Scammells, Green Chem. 7, 9 (2007)

    Article  Google Scholar 

  25. R. Franzen, Comb. Chem. 2, 195 (2000)

    Article  CAS  Google Scholar 

  26. M.H. Valkenberg, C. deCastro, W.F. Hölderich, Green Chem. 4, 88 (2002)

    Article  CAS  Google Scholar 

  27. E. Benazzi, A. Hirschauer, J.F. Joly, H. Olivier, J.Y. Berhard, Eur. Patent EP 0,553,009 28, 7 (1993)

    Google Scholar 

  28. C.P. Mehnert, Chem. Eur. J. 11, 50 (2004)

    Article  CAS  Google Scholar 

  29. A. Riisager, B. Jørgensen, P. Wasserscheid, R. Fehrmann, Chem. Commun. 994 (2006)

  30. R. Sugimura, K. Qiao, D. Tomida, C. Yokoyama, Catal. Commun. 8, 770 (2007)

    Article  CAS  Google Scholar 

  31. J.Q. Wang, X.D. Yue, F. Cai, L.N. He, Catal. Commun. 8, 167 (2007)

    Article  CAS  Google Scholar 

  32. M.J. Jin, A. Taher, H.J. Kang, M. Choi, R. Ryoo, Green Chem. 11, 309 (2009)

    Article  CAS  Google Scholar 

  33. P.R. Likhar, S. Roy, M. Roy, M.S. Subhas, M. Lakshmi Kantam, Catal. Commun. 10, 728 (2009)

    Article  CAS  Google Scholar 

  34. M.I. Burguete, H. Erytropel, E.G. Verdugo, S.V. Luis, V. Sans, Green Chem. 10, 401 (2008)

    Article  CAS  Google Scholar 

  35. M. Mamaghani, A. Loghmanifar, M.R. Taati, Ultrason. Sonochem. 18, 45 (2011)

    Article  CAS  Google Scholar 

  36. M. Nikpassand, M. Mamaghani, F. Shirini, K. Tabatabaeian, Ultrason. Sonochem. 17, 301 (2010)

    Article  CAS  Google Scholar 

  37. M. Mamaghani, N.O. Mahmoodi, S. Fallah Ghassemi, J. Iran. Chem. Soc. 7, 972 (2010)

    CAS  Google Scholar 

  38. M. Mamaghani, S. Dastmard, Arkivoc 168 (2009)

  39. H.A. Samimi, M. Mamaghani, K. Tabatabaeian, Heterocycles 75, 2825 (2008)

    Article  CAS  Google Scholar 

  40. H.A. Samimi, M. Mamaghani, K. Tabatabaeian, J. Heterocycl. Chem. 45, 1765 (2008)

    Article  CAS  Google Scholar 

  41. K. Tabatabaeian, M. Mamaghani, N. Mahmoodi, A. Khorshidi, J. Mol. Catal. A 270, 112 (2007)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful to the Research Council of University of Guilan for the financial support of this research work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Guilan, P.O. Box 41335-1914, Rasht, Iran

    Maryam Saffari Jourshari, Manouchehr Mamaghani, Khalil Tabatabaeian & Farhad Shirini

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  1. Maryam Saffari Jourshari
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  2. Manouchehr Mamaghani
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  3. Khalil Tabatabaeian
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  4. Farhad Shirini
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Correspondence to Manouchehr Mamaghani.

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Saffari Jourshari, M., Mamaghani, M., Tabatabaeian, K. et al. A convenient synthesis of novel 5-arylidene-2-imino-4-thiazolidinones using base supported ionic liquid-like phase (SILLP) as efficient green catalyst. J IRAN CHEM SOC 9, 75–80 (2012). https://doi.org/10.1007/s13738-011-0012-0

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