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A one-pot multi-component reaction for the facile synthesis of some novel 2-aryl thiazolidinones bearing benzimidazole moiety using La(NO3)3·6H2O as an efficient catalyst

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Abstract

A series of new derivatives of 3-benzimidazolyl-2-aryl thiazolidinones, 4a–j are synthesized via a rapid, one-pot, three-component reaction by using La(NO3)3·6H2O as an efficient catalyst from the reaction of 2-aminobenzimidazole, aromatic aldehydes and thioglycolic acid in ethanol at room temperature. These new compounds were characterized by IR, 1H, 13C NMR and mass spectroscopies. An inexpensive and available catalyst, short reaction time, easy workup, good to excellent yields and nontoxic solvent are the advantages of this reaction.

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References

  1. L. Weber, Drug Discov. Today 7, 143–147 (2002)

    Article  CAS  Google Scholar 

  2. J.C. Menendez, Synthesis 15, 2624 (2006). doi:10.1055/s-2006-949153

    Article  Google Scholar 

  3. M.J. Climent, A. Corma, S. Iborra, RSC Adv. 2, 16–58 (2012)

    Article  CAS  Google Scholar 

  4. S. Pola, Signif. Thiazole-based Heterocycles Bioact. Syst. (2016). doi:10.5772/62077

    Google Scholar 

  5. T. Kvernmo, S. Härtter, E. Burger, Clin. Ther. 28, 1065–1078 (2006)

    Article  CAS  Google Scholar 

  6. A.K. Jain, A. Vaidya, V. Ravichandran, S.K. Kashaw, R.K. Agraval, Bioorg. Med. Chem. 20, 3378–3395 (2012). and references cited therein

    Article  CAS  Google Scholar 

  7. R.V. Patel, S.W. Park, Res. Chem. Intermed. 41, 5599–5609 (2015)

    Article  CAS  Google Scholar 

  8. P.D. Neuenfeldt, B.B. Drawanz, G.M. Siqueira, C.R.B. Gomes, S. Wardell, A.F.C. Flores, W. Cunico, Tetrahedron Lett. 51, 3106–3108 (2010)

    Article  CAS  Google Scholar 

  9. A.N. Solankee, K.P. Patel, R.B. Patel, Adv. Appl. Sci. Res. 3, 117–122 (2012)

    CAS  Google Scholar 

  10. A. Rao, A. Chimirri, S. Ferro, A.M. Monforte, P. Monforte, M. Zappalà, Arkivoc 5, 147–155 (2004)

    Google Scholar 

  11. A. Mobinikhaledi, N. Forughifar, M. Kalhor, M. Mirabolfathy, J. Heterocyclic Chem. 47, 77–80 (2010)

    CAS  Google Scholar 

  12. T. Srivastava, W. Haq, S.B. Katti, Tetrahedron 58, 7619–7624 (2002). and references cited therein

    Article  CAS  Google Scholar 

  13. N. Foroughifar, S. Ebrahimi, Chin. Chem. Lett. 24, 389–391 (2013)

    Article  CAS  Google Scholar 

  14. M.P. Thakare, P. Kumar, N. Kumar, S.K. Pandey, Tetrahedron Lett. 55, 2463–2466 (2014)

    Article  CAS  Google Scholar 

  15. H.X. Pang, Y.H. Hui, K. Fan, X.J. Xing, Y. Wu, J.H. Yang, W. Shi, Z.F. Xie, Chin. Chem. Lett. 27, 335–339 (2016)

    Article  CAS  Google Scholar 

  16. A.V. Chate, A.G. Tathe, P.J. Nagtilak, S.M. Sangle, C.H. Gill, Chin.Chem. Catal. 37, 1997–2002 (2016)

    Article  CAS  Google Scholar 

  17. R.R. Harale, P.V. Shitre, B.R. Sathe, M.S. Shingare, Res. Chem. Intermed. 42, 6695–6703 (2016)

    Article  CAS  Google Scholar 

  18. M.P. Thakare, R. Shaikh, D. Tayade, RSC Adv. 6, 28619–28623 (2016)

    Article  CAS  Google Scholar 

  19. S.M. Sadeghzadeh, M. Malekzadeh, J. Mol. Liq. 202, 46–51 (2015)

    Article  CAS  Google Scholar 

  20. A.K. Yadav, M. Kumar, T. Yadav, R. Jain, Tetrahedron Lett. 50, 5031–5034 (2009)

    Article  CAS  Google Scholar 

  21. S.A. Jadhav, M.G. Shioorkar, O.S. Chavan, D.B. Shinde, R.K. Pardeshi, Heterocyclic Lett. 5, 375–382 (2015)

    CAS  Google Scholar 

  22. C. Jun, X. Jiangtao, L. Xianjin, Bioorg. Med. Chem. Lett. 15, 267–269 (2005)

    Article  Google Scholar 

  23. K.T. Ashish, M. Anil, Ind. Chem. 45, 489–493 (2006)

    Google Scholar 

  24. E. Carlsson, P. Lindberg, S. Unge, Chem. Br. 38, 42–45 (2002)

    CAS  Google Scholar 

  25. M.E. Hassan, M.B. Alaa-eldin, M.B. Sahas, A.A. Farahat, Ind. J. Chem. 49, 1515–1525 (2010)

    Google Scholar 

  26. A.K. Gu¨lgu¨, A. Nurten, Farmaco 58, 1345–1350 (2003)

    Article  Google Scholar 

  27. Y.L. Luo, K. Baathulaa, V.K. Kannekanti, C.H. Zhou, G.X. Cai, Sci. China Chem. 58, 483–494 (2015)

    Article  CAS  Google Scholar 

  28. H.Z. Zhang, J.M. Lin, S. Rashid, C.H. Zou, Sci. China Chem. 57, 807–822 (2014)

    Article  CAS  Google Scholar 

  29. W. Maxwell, G. Brody, App. Microbial 21, 944–945 (1971)

    CAS  Google Scholar 

  30. A.K. G¨ulg¨un, A. Nurten, Turk. J. Chem. 30, 223–228 (2006)

    Google Scholar 

  31. E.S. Lazer, M.R. Matteo, G.J. Possanza, J. Med. Chem. 30, 726–729 (1987)

    Article  CAS  Google Scholar 

  32. L. Srikanth, N. Raghunandan, R. Sambasiva, Der Pharma. Chemic. 3, 344–352 (2011)

    Google Scholar 

  33. K. Sreena, R. Ratheesh, M. Rachana, M. Poornima, C. Shyni, Hygei 1, 21–22 (2009)

    Google Scholar 

  34. A. Mobinikhaledi, N. Forughifar, M. Kalhor, Syn. React. Inorg. Met-org. Chem. 39, 509–511 (2009)

    CAS  Google Scholar 

  35. K.U. Sadek, F. Al-Qalaf, R.A. Mekheimer, M.H. Elnagdi, Arabian J. Chem. 5, 63–66 (2010)

    Article  Google Scholar 

  36. M.M. Ramla, M.A. Omar, H. Tokuda, H.I. El-Diwoni, Bioorg. Med. Chem. 15, 64896496 (2007)

    Article  Google Scholar 

  37. Z. Kazimierczuk, D. Shugar, Nucleosides Nucleotides 8, 1379–1385 (1989)

    Article  CAS  Google Scholar 

  38. M. Kalhor, Org. Chem. Res. 1, 59–65 (2015)

    Google Scholar 

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Acknowledgement

We are grateful for the research commute of Chemistry Department of Payame Noor University for providing financial and technical support of this work.

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Correspondence to Mehdi Kalhor.

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Kalhor, M., Banibairami, S. & Mirshokraie, S.A. A one-pot multi-component reaction for the facile synthesis of some novel 2-aryl thiazolidinones bearing benzimidazole moiety using La(NO3)3·6H2O as an efficient catalyst. Res Chem Intermed 43, 5985–5994 (2017). https://doi.org/10.1007/s11164-017-2974-8

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  • DOI: https://doi.org/10.1007/s11164-017-2974-8

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