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Microwave Assisted Synthesis of 1,5-Benzothiazepines Using Greener Reaction Medium
Corresponding Author(s) : Vasant B. Jagrut
Asian Journal of Chemistry,
Vol. 31 No. 5 (2019): Vol 31 Issue 5
Abstract
An efficient and eco-friendly synthesis of 1,5-benzothiazepines has been developed by the reaction of various 2-propen-1-ones with 2-aminothiophenol using microwave irradiation in greener reaction medium, glycerol. The clean reaction conditions, shorter reaction time, high yields and non-toxic, biodegradable reaction medium manufactured from renewable sources are unique features of this method.
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References
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G. Grandolini, Eur. J. Med. Chem., 34, 701 (1999); https://doi.org/10.1016/S0223-5234(99)00223-8.
M.J. Urbanski, R.H. Chen, K.T. Demarest, J. Gunnet, R. Look, E. Ericson, W.V. Murray, P.J. Rybczynski and X. Zhang, Bioorg. Med. Chem. Lett., 13, 4031 (2003); https://doi.org/10.1016/j.bmcl.2003.08.051.
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L.P. Tardibono and M.J. Miller, Org. Lett., 11, 1575 (2009); https://doi.org/10.1021/ol900210h.
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F. Micheli, F. Degiorgis, A. Feriani, A. Paio, A. Pozzan, P. Zarantonello and P.J. Seneci, Comb. Chem., 3, 224 (2001); https://doi.org/10.1021/cc0000949.
S. Pant, B. Singhal, M. Upreti and U. Pant, Molecules, 3, 159 (1998); https://doi.org/10.3390/30600159.
M. Upreti, S. Pant, A. Dandia and U.C. Pant, Indian J. Chem., 36B, 1181 (1997).
M. Kodomari, T. Noguchi and T. Aoyama, Synth. Commun., 34, 1783 (2004); https://doi.org/10.1081/SCC-120034159.
G. Sharma, R. Kumar and A.K. Chakraborti, Tetrahedron Lett., 49, 4272 (2008); https://doi.org/10.1016/j.tetlet.2008.04.144.
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M. Kodomari, T. Noguchi and T. Aoyama, Synth. Commun., 34, 1783 (2004); https://doi.org/10.1081/SCC-120034159.
R.K. Saini, Y.C. Joshi and P. Joshi, Phosphorus Sulfur Silicon Relat. Elem., 183, 2181 (2008); https://doi.org/10.1080/10426500701852661.
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R.J. Giguere, T.L. Bray, S.M. Duncan and G. Majetich, Tetrahedron Lett., 27, 4945 (1986); https://doi.org/10.1016/S0040-4039(00)85103-5.
M.B. Gawande, V.D.B. Bonifacio, R. Luque, P.S. Branco and R.S. Varma, Chem. Soc. Rev., 42, 5522 (2013); https://doi.org/10.1039/c3cs60025d.
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V. Polshettiwar and R.S. Varma, Chem. Soc. Rev., 37, 1546 (2008); https://doi.org/10.1039/b716534j.
M.B. Gawande and P.S. Branco, Green Chem., 13, 3355 (2011); https://doi.org/10.1039/c1gc15868f.
V. Polshettiwar and R.S. Varma, J. Org. Chem., 72, 7420 (2007); https://doi.org/10.1021/jo701337j.
D.M.L. Cabrera, F.M. Líbero, D. Alves, G. Perin, E.J. Lenardão and R.G. Jacob, Green Chem. Lett. Rev., 5, 329 (2012); https://doi.org/10.1080/17518253.2011.631942.
P.D. Netankar, D.L. Lingampalle, V.B. Jagrut, D.V. Jawale and R.A. Mane, Chem. Biol. Interf., 2, 246 (2012);
V.B. Jagrut, D.L. Lingampalle, R.P. Phase and W.N. Jadhav, J. Chem. Biol. Phys. Sci. Sec. A., 2, 1166 (2012).
V.B. Jagrut, D.L. Lingampalle, P.D. Netankar and W.N. Jadhav, Der Pharma Chemica, 5, 8 (2013).
D.L. Lingampalle, P.D. Netankar, V.B. Jagrut and R.A. Mane, Chem. Biol. Interf.., 4, 287 (2014).
V.B. Jagrut, D.L. Lingampalle, R.A. Mane and W.N. Jadhav, J. Chem. Pharm. Res., 4, 3121 (2012).
G. Sharma, R. Kumar and A.K. Chakraborti, Tetrahedron Lett., 49, 4269 (2008); https://doi.org/10.1016/j.tetlet.2008.04.146.