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Green approach: an efficient synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles in aqueous medium under ultrasonic irradiation

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Abstract

An efficient and rapid procedure for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles has been described by the reaction of α-bromoketones with thiourea, phenylthiourea and selenourea at ambient temperature in aqueous medium under ultrasonic irradiation. Analytically pure products were formed within 10–60 s in excellent yields. The advantageous features of this non-conventional methodology over conventional methods are the operational simplicity, easy handling, yield-enhancing, time-reducing, mild reaction conditions and no by-product production.

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References

  1. A. Iskalieva, B.M. Yimmou, P.R. Gogate, M. Horvath, P.G. Horvath, L. Csoka, Ultrason. Sonochem. 19, 984 (2012)

    Article  CAS  Google Scholar 

  2. C. Einhorn, J. Einhorn, J.-L. Luche, Synthesis 11, 787 (1989)

    Article  Google Scholar 

  3. J.T. Li, S.X. Wang, G.F. Chen, Curr. Org. Synth. 2, 415 (2005)

    Article  CAS  Google Scholar 

  4. L. Jianjun, L. Jia, F. Jin, S. Weike, Synth. Commun. 40, 1029 (2010)

    Article  Google Scholar 

  5. V.N. Telvekar, K.A. Sasane, Synth. Commun. 42, 1085 (2012)

    Article  CAS  Google Scholar 

  6. E.L. Luzina, A.V. Popov, Eur. J. Med. Chem. 44, 4944 (2009)

    Article  CAS  Google Scholar 

  7. 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 

  8. A. Cohen, P. Verhaeghe, M.D. Crozet, S. Hutter, P. Rathelot, P. Vanelle, N. Azas, Eur. J. Med. Chem. 55, 315 (2012)

    Article  CAS  Google Scholar 

  9. K. Brown, D.P. Cater, J.F. Cavalla, D. Green, R.A. Newberry, A.B. Wilson, J. Med. Chem. 17, 1177 (1974)

    Article  CAS  Google Scholar 

  10. K. Tsuji, H. Ishikawa, Bioorg. Med. Chem. Lett. 4, 1601 (1994)

    Article  CAS  Google Scholar 

  11. W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G. Taylor Jr, C.J.C. Connolly, A.M. Doherty, S.R. Klutchko, I. Sircar, B.A. Steinbaugh, B.L. Batley, C.A. Painchaud, S.T. Rapundalo, B.M. Michniewicz, S.C. Olson, J. Med. Chem. 35, 2562 (1992)

    Article  CAS  Google Scholar 

  12. P.J. Islip, M.D. Closier, M.C. Neville, J. Med. Chem. 17, 207 (1974)

    Article  CAS  Google Scholar 

  13. F.W. Bell, A.S. Cantrell, M. Hoegberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordon, M.D. Kinnick, P. Lind, J.M. Morin Jr, R. Noreen, B. Oberg, J.A. Palkowitz, C.A. Parrish, P. Pranc, C. Sahlberg, R.J. Ternansky, R.T. Vasileff, L. Vrang, S.J. West, H. Zhang, X.-X. Zhou, J. Med. Chem. 38, 4929 (1995)

    Article  CAS  Google Scholar 

  14. G.H. Shridhar, D.M. Martin, J. Agric. Food Chem. 41, 2131 (1993)

    Article  Google Scholar 

  15. B.A. Fink, D.S. Mortensen, S.R. Stauffer, Z.D. Aron, J.A. Katzenellenbogen, Chem. Biol. 6, 205 (1999)

    Article  CAS  Google Scholar 

  16. J.E. Van Muijlwijk-Koezen, H. Timmerman, R.C. Vollinga, J.F. Von Drabbe Kunzel, M. DeGroote, S. Visser, A.P. Ijzerman, J. Med. Chem. 44, 749 (2001)

    Article  Google Scholar 

  17. A. Mori, A. Sekiguchi, K. Masui, T. Shimada, M. Horie, K. Osakada, M. Kawamoto, T. Ikeda, J. Am. Chem. Soc. 125, 1700 (2003)

    Article  CAS  Google Scholar 

  18. K. Dolling, H. Zaschke, H. Schubert, J. Prakt. Chem. 321, 643 (1979)

    Article  Google Scholar 

  19. P. Vicini, A. Geronikaki, M. Incerti, F. Zani, J. Dearden, M. Hewitt, Bioorg. Med. Chem. 16, 3714 (2008)

    Article  CAS  Google Scholar 

  20. G. Gebeyehu, V.E. Marquez, A.V. Cott, J. Med. Chem. 28, 99 (1985)

    Article  CAS  Google Scholar 

  21. Y. Kumar, R. Green, D.S. Wise, L.L. Wotring, L.B. Townsend, J. Med. Chem. 36, 3849 (1993)

    Article  CAS  Google Scholar 

  22. A. Nishina, H. Kimura, K. Kozawa, G.L. Sommen, T. Nakamura, H. Heimgartner, M. Koketsu, S. Furukawa, Toxicol. Appl. Pharmacol. 257, 388 (2011)

    Article  CAS  Google Scholar 

  23. A. Nishina, A. Sekiguchi, R.H. Fukumoto, M. Koketsu, S. Furukawa, Biochem Biophys. Res. Commun. 352, 360 (2007)

    Article  CAS  Google Scholar 

  24. N.T. Akbaraly, J. Arnaud, I. Hininger-Favier, V. Gourlet, A.M. Roussel, C. Berr, Clin. Chem. 51, 2117 (2005)

    Article  CAS  Google Scholar 

  25. B. Das, V. Saidi Reddy, R. Ramu, J. Mol. Catal. A Chem. 252, 235 (2006)

    Article  CAS  Google Scholar 

  26. M. Narender, M.S. Reddy, V.P. Kumar, V.P. Reddy, Y.V.D. Nageswar, K.R. Rao, J. Org. Chem. 72, 1849 (2007)

    Article  CAS  Google Scholar 

  27. D. Anshu, K.J. Anuj, S.B. Dharmendra, Synth. Commun. 41, 2905 (2011)

    Article  Google Scholar 

  28. B. Umadevi, Eur. J. Med. Chem. 42, 1144 (2007)

    Article  Google Scholar 

  29. M.A. Gouda, M.A. Berghot, E.A. Baz, W.S. Hamama, Med. Chem. Res. 21, 1062 (2012)

    Article  CAS  Google Scholar 

  30. K. Ninomiya, A. Fukuda, C. Ogino, N. Shimizu, Ultrason. Sonochem. 21, 1624 (2014)

    Article  CAS  Google Scholar 

  31. J.V. Madhav, B.S. Kuarm, B. Rajitha, Synth. Commun. 38, 3514 (2008)

    Article  CAS  Google Scholar 

  32. M. Mirza-Aghayana, E. Kashef-Azar, R. Boukherroub, Tetrahedron Lett. 53, 4962 (2012)

    Article  Google Scholar 

  33. H. Karade, M. Sathe, M.P. Kaushik, Catal. Commun. 8, 741 (2007)

    Article  CAS  Google Scholar 

  34. T.M. Potewar, S.A. Ingale, K.V. Srinivasan, Arkivoc 12, 117 (2008)

    Google Scholar 

  35. D. Zhu, J. Chen, H. Xiao, M. Liu, J. Ding, H. Wu, Synth. Commun. 39, 2895 (2009)

    Article  CAS  Google Scholar 

  36. A.V. Narsaiah, R.S. Ghogare, D.O. Biradar, Org. Commun. 4, 75 (2011)

    Google Scholar 

  37. T.M. Potewar, S.A. Ingale, K.V. Srinivasan, Tetrahedron 64, 5019 (2008)

    Article  CAS  Google Scholar 

  38. B. Janardhan, G. Rajitha, V. Ravibabu, B. Rajitha, J. Chem. Sci. 125, 843 (2013)

    Article  Google Scholar 

  39. A. Gursoy, N. Karali, Turk. J. Chem. 27, 545 (2003)

    Google Scholar 

  40. B. Janardhan, V. Krishnaiah, B. Rajitha, P.A. Crooks, Chin. Chem. Lett. 25, 172 (2014)

    Article  Google Scholar 

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Acknowledgments

We would like to thank the Director, National Institute of Technology, Warangal for providing research facilities. One of the authors R.G. thanks the Ministry of Human Resource Development for financial support.

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Correspondence to Banothu Janardhan.

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Ramesh, G., Janardhan, B. & Rajitha, B. Green approach: an efficient synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles in aqueous medium under ultrasonic irradiation. Res Chem Intermed 41, 8099–8109 (2015). https://doi.org/10.1007/s11164-014-1879-z

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  • DOI: https://doi.org/10.1007/s11164-014-1879-z

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