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A Convenient and Benign Synthesis of Sulphonamides in PEG-400
Corresponding Author(s) : Pranab Jyoti Das
Asian Journal of Chemistry,
Vol. 27 No. 1 (2015): Vol 27 Issue 1
Abstract
A simple and convenient method is reported for the synthesis of a series of sulphonamides in PEG-400 using potassium carbonate as the base. The reaction is carried out in a heterogeneous medium and consequently product recovery is simple. The desired products with a variety of aromatic amines could be synthesized in a short reaction time in good yield. The PEG could be recovered for reuse.
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- S. Chandrasekhar, S.J. Prakash and C.L. Rao, J. Org. Chem., 71, 2196 (2006); doi:10.1021/jo052604x.
- W.-J. Liu, Y.-X. Xie, Y. Liang and J.-H. Li, Synthesis, 860 (2006); doi:10.1055/s-2006-926323.
- R. Ballini, L. Barboni and A. Palmieri, Green Chem., 10, 1004 (2008); doi:10.1039/b805985c.
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- N.Y. Sreedhar and M.R. Jayapal, Res. J. Pharm. Biol. Chem. Sci., 1, 480 (2010).
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- X. Wang, H. Gong, V. Quan, L. Li and H. Ye, Synth. Commun., 41, 3251 (2011); doi:10.1080/00397911.2010.517888.
- M. Remko and C.-W. von der Lieth, Bioorg. Med. Chem., 12, 5395 (2004); doi:10.1016/j.bmc.2004.07.049.
- N.S. El-Sayed, E.R. El-Bendary, S.M. El-Ashry and M.M. El-Kerdawy, Eur. J. Med. Chem., 46, 3714 (2011); doi:10.1016/j.ejmech.2011.05.037.
- M.J. García-Galán, M. Silvia Díaz-Cruz and D. Barceló, Trends Analyt. Chem., 27, 1008 (2008); doi:10.1016/j.trac.2008.10.001.
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- M.C. Marcotullio, V. Campagna, S. Sternativo, V. Costantino and M. Curini, Synthesis, 2760 (2006); doi:10.1055/s-2006-942488.
- X. Yu, C. Liu, L. Jiang and Q. Xu, Org. Lett., 13, 6184 (2011); doi:10.1021/ol202582c.
- B.R. Rosen, J.C. Ruble, T.J. Beauchamp and A. Navarro, Org. Lett., 13, 2564 (2011); doi:10.1021/ol200660s.
- D.M.T. Chan, K.L. Monaco, R.-P. Wang and M.P. Winters, Tetrahedron Lett., 39, 2933 (1998); doi:10.1016/S0040-4039(98)00503-6.
- R. Bhuyan and K.M. Nicholas, Org. Lett., 9, 3957 (2007); doi:10.1021/ol701544z.
- M.M. Zhao, C. Qu and J.E. Lynch, J. Org. Chem., 70, 6944 (2005); doi:10.1021/jo050500g.
- D.C. Reuter, J.E. McIntosh, A.C. Guinn and A.M. Madera, Synthesis, 2321 (2003); doi:10.1055/s-2003-41059.
- M.H.S.A. Hamid, C.L. Allen, G.W. Lamb, A.C. Maxwell, H.C. Maytum, A.J.A. Watson and J.M.J. Williams, J. Am. Chem. Soc., 131, 1766 (2009); doi:10.1021/ja807323a.
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References
S. Chandrasekhar, S.J. Prakash and C.L. Rao, J. Org. Chem., 71, 2196 (2006); doi:10.1021/jo052604x.
W.-J. Liu, Y.-X. Xie, Y. Liang and J.-H. Li, Synthesis, 860 (2006); doi:10.1055/s-2006-926323.
R. Ballini, L. Barboni and A. Palmieri, Green Chem., 10, 1004 (2008); doi:10.1039/b805985c.
S. Chandrasekhar, C. Narsihmulu, G. Chandrashekar and T. Shyamsunder, Tetrahedron Lett., 45, 2421 (2004); doi:10.1016/j.tetlet.2004.01.097.
N.Y. Sreedhar and M.R. Jayapal, Res. J. Pharm. Biol. Chem. Sci., 1, 480 (2010).
D. Kumar, G. Patel, B.G. Mishra and R.S. Varma, Tetrahedron Lett., 49, 6974 (2008); doi:10.1016/j.tetlet.2008.09.116.
N.V. Shitole, K.F. Shelke, S.A. Sadaphal, B.B. Shingate and M.S. Shingare, Green Chem Lett. Rev, 3, 83 (2010); doi:10.1080/17518250903567246.
J. Liang, J. Lv and Z. Shang, Tetrahedron, 67, 8532 (2011); doi:10.1016/j.tet.2011.08.091.
X. Wang, H. Gong, V. Quan, L. Li and H. Ye, Synth. Commun., 41, 3251 (2011); doi:10.1080/00397911.2010.517888.
M. Remko and C.-W. von der Lieth, Bioorg. Med. Chem., 12, 5395 (2004); doi:10.1016/j.bmc.2004.07.049.
N.S. El-Sayed, E.R. El-Bendary, S.M. El-Ashry and M.M. El-Kerdawy, Eur. J. Med. Chem., 46, 3714 (2011); doi:10.1016/j.ejmech.2011.05.037.
M.J. García-Galán, M. Silvia Díaz-Cruz and D. Barceló, Trends Analyt. Chem., 27, 1008 (2008); doi:10.1016/j.trac.2008.10.001.
G.L. Perlovich, N.N. Strakhova, V.P. Kazachenko, T.V. Volkova, V.V. Tkachev, K.-J. Schaper and O.A. Raevsky, Int. J. Pharm., 349, 300 (2008); doi:10.1016/j.ijpharm.2007.07.034.
W. Luo, Q.- Yu, S.S. Kulkarni, D.A. Parrish, H.W. Holloway, D. Tweedie, A. Shafferman, D.K. Lahiri, A. Brossi and N.H. Greig, J. Med. Chem., 49, 2174 (2006); doi:10.1021/jm050578p.
M.C. Marcotullio, V. Campagna, S. Sternativo, V. Costantino and M. Curini, Synthesis, 2760 (2006); doi:10.1055/s-2006-942488.
X. Yu, C. Liu, L. Jiang and Q. Xu, Org. Lett., 13, 6184 (2011); doi:10.1021/ol202582c.
B.R. Rosen, J.C. Ruble, T.J. Beauchamp and A. Navarro, Org. Lett., 13, 2564 (2011); doi:10.1021/ol200660s.
D.M.T. Chan, K.L. Monaco, R.-P. Wang and M.P. Winters, Tetrahedron Lett., 39, 2933 (1998); doi:10.1016/S0040-4039(98)00503-6.
R. Bhuyan and K.M. Nicholas, Org. Lett., 9, 3957 (2007); doi:10.1021/ol701544z.
M.M. Zhao, C. Qu and J.E. Lynch, J. Org. Chem., 70, 6944 (2005); doi:10.1021/jo050500g.
D.C. Reuter, J.E. McIntosh, A.C. Guinn and A.M. Madera, Synthesis, 2321 (2003); doi:10.1055/s-2003-41059.
M.H.S.A. Hamid, C.L. Allen, G.W. Lamb, A.C. Maxwell, H.C. Maytum, A.J.A. Watson and J.M.J. Williams, J. Am. Chem. Soc., 131, 1766 (2009); doi:10.1021/ja807323a.
V.K. Ahluwalia and S. Dhingra, Comprehensive Practical Organic Chemistry, University Press, New Delhi, pp. 218-220 (2000).
A.I. Vogel, A Textbook of Practical Organic Chemistry, ELBS/Longman, London, edn 5 (1989).