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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A. Iskalieva, B.M. Yimmou, P.R. Gogate, M. Horvath, P.G. Horvath, L. Csoka, Ultrason. Sonochem. 19, 984 (2012)
C. Einhorn, J. Einhorn, J.-L. Luche, Synthesis 11, 787 (1989)
J.T. Li, S.X. Wang, G.F. Chen, Curr. Org. Synth. 2, 415 (2005)
L. Jianjun, L. Jia, F. Jin, S. Weike, Synth. Commun. 40, 1029 (2010)
V.N. Telvekar, K.A. Sasane, Synth. Commun. 42, 1085 (2012)
E.L. Luzina, A.V. Popov, Eur. J. Med. Chem. 44, 4944 (2009)
J. Cai, M. Sun, X. Wu, J. Chen, P. Wang, X. Zong, M. Ji, Eur. J. Med. Chem. 63, 702 (2013)
A. Cohen, P. Verhaeghe, M.D. Crozet, S. Hutter, P. Rathelot, P. Vanelle, N. Azas, Eur. J. Med. Chem. 55, 315 (2012)
K. Brown, D.P. Cater, J.F. Cavalla, D. Green, R.A. Newberry, A.B. Wilson, J. Med. Chem. 17, 1177 (1974)
K. Tsuji, H. Ishikawa, Bioorg. Med. Chem. Lett. 4, 1601 (1994)
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)
P.J. Islip, M.D. Closier, M.C. Neville, J. Med. Chem. 17, 207 (1974)
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)
G.H. Shridhar, D.M. Martin, J. Agric. Food Chem. 41, 2131 (1993)
B.A. Fink, D.S. Mortensen, S.R. Stauffer, Z.D. Aron, J.A. Katzenellenbogen, Chem. Biol. 6, 205 (1999)
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)
A. Mori, A. Sekiguchi, K. Masui, T. Shimada, M. Horie, K. Osakada, M. Kawamoto, T. Ikeda, J. Am. Chem. Soc. 125, 1700 (2003)
K. Dolling, H. Zaschke, H. Schubert, J. Prakt. Chem. 321, 643 (1979)
P. Vicini, A. Geronikaki, M. Incerti, F. Zani, J. Dearden, M. Hewitt, Bioorg. Med. Chem. 16, 3714 (2008)
G. Gebeyehu, V.E. Marquez, A.V. Cott, J. Med. Chem. 28, 99 (1985)
Y. Kumar, R. Green, D.S. Wise, L.L. Wotring, L.B. Townsend, J. Med. Chem. 36, 3849 (1993)
A. Nishina, H. Kimura, K. Kozawa, G.L. Sommen, T. Nakamura, H. Heimgartner, M. Koketsu, S. Furukawa, Toxicol. Appl. Pharmacol. 257, 388 (2011)
A. Nishina, A. Sekiguchi, R.H. Fukumoto, M. Koketsu, S. Furukawa, Biochem Biophys. Res. Commun. 352, 360 (2007)
N.T. Akbaraly, J. Arnaud, I. Hininger-Favier, V. Gourlet, A.M. Roussel, C. Berr, Clin. Chem. 51, 2117 (2005)
B. Das, V. Saidi Reddy, R. Ramu, J. Mol. Catal. A Chem. 252, 235 (2006)
M. Narender, M.S. Reddy, V.P. Kumar, V.P. Reddy, Y.V.D. Nageswar, K.R. Rao, J. Org. Chem. 72, 1849 (2007)
D. Anshu, K.J. Anuj, S.B. Dharmendra, Synth. Commun. 41, 2905 (2011)
B. Umadevi, Eur. J. Med. Chem. 42, 1144 (2007)
M.A. Gouda, M.A. Berghot, E.A. Baz, W.S. Hamama, Med. Chem. Res. 21, 1062 (2012)
K. Ninomiya, A. Fukuda, C. Ogino, N. Shimizu, Ultrason. Sonochem. 21, 1624 (2014)
J.V. Madhav, B.S. Kuarm, B. Rajitha, Synth. Commun. 38, 3514 (2008)
M. Mirza-Aghayana, E. Kashef-Azar, R. Boukherroub, Tetrahedron Lett. 53, 4962 (2012)
H. Karade, M. Sathe, M.P. Kaushik, Catal. Commun. 8, 741 (2007)
T.M. Potewar, S.A. Ingale, K.V. Srinivasan, Arkivoc 12, 117 (2008)
D. Zhu, J. Chen, H. Xiao, M. Liu, J. Ding, H. Wu, Synth. Commun. 39, 2895 (2009)
A.V. Narsaiah, R.S. Ghogare, D.O. Biradar, Org. Commun. 4, 75 (2011)
T.M. Potewar, S.A. Ingale, K.V. Srinivasan, Tetrahedron 64, 5019 (2008)
B. Janardhan, G. Rajitha, V. Ravibabu, B. Rajitha, J. Chem. Sci. 125, 843 (2013)
A. Gursoy, N. Karali, Turk. J. Chem. 27, 545 (2003)
B. Janardhan, V. Krishnaiah, B. Rajitha, P.A. Crooks, Chin. Chem. Lett. 25, 172 (2014)
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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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