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Di-cationic Ionic Liquid Catalyzed Synthesis of 1,5-Benzothiazepines
Corresponding Author(s) : Raghavendra Sakirolla
Asian Journal of Chemistry,
Vol. 30 No. 1 (2018): Vol 30 Issue 1
Abstract
A simple and elegant method for the synthesis of 1,5-benzothiazepines has been developed using di-cationic liquid as a solvent cum catalyst by the reaction of o-aminothiophenol with a variety of chalcones under mild reaction conditions. Furthermore the reusability of the catalyst has also been studied for three cycles. All the reactions are proposed to proceed through a 1,4-conjugate Michael addition followed by a cyclo-condensation reaction.
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References
J.R. Reddy and P.N. Sharma, Indian J. Chem., 32B, 404 (1993).
S. Ohno, K. Izumi, K. Mizukoshi, K. Kato and M. Hori, Chem. Pharm. Bull. (Tokyo), 31, 1780 (1983); https://doi.org/10.1248/cpb.31.1780.
M. Chiesi, R. Schwaller and K. Eichenberger, Biochem. Pharmacol., 37, 4399 (1988); https://doi.org/10.1016/0006-2952(88)90623-5.
K.V.V. Reddy, P.S. Rao and D. Ashok, Synth. Commun., 30, 1825 (2000); https://doi.org/10.1080/00397910008087228.
W. Ried and E. Torinus, Chem. Ber., 92, 2902 (1959); https://doi.org/10.1002/cber.19590921138.
W. Ried and P. Stahlhofen, Chem. Ber., 90, 815 (1957); https://doi.org/10.1002/cber.19570900528.
J.A.L. Herbert and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 2657 (1974); https://doi.org/10.1039/p19740002657.
R. Contreras, H. R. Morales and A. Bulbarela,Heterocycles, 24, 135 (1986); https://doi.org/10.3987/R-1986-01-0135.
J.S. Yadav, B.V.S. Reddy, B. Eshwaraiah and K. Anuradha, Green Chem., 4, 592 (2002); https://doi.org/10.1039/B206558B.
M.E.F. Curini, F. Epifano, M.C. Marcotullio and O. Rosati, Tetrahedron Lett., 42, 3193 (2001); https://doi.org/10.1016/S0040-4039(01)00413-0.
X.Q. Pan, J.P. Zou, Z.H. Huang and W. Zhang, Tetrahedron Lett., 49, 5302 (2008); https://doi.org/10.1016/j.tetlet.2008.06.082.
M. Pozarentzi, J. Stephanidou-Stephanatou and C.A. Tsoleridis,Tetrahedron Lett., 43, 1755 (2002); https://doi.org/10.1016/S0040-4039(02)00115-6.
C.-W.M. Kuo, S.V. More and C.-F. Yao, Tetrahedron Lett., 47, 8523 (2006); https://doi.org/10.1016/j.tetlet.2006.09.128.
F.L. Ansari, S. Umbreen, L. Hussain, T. Makhmoor, S.A. Nawaz, M.A. Lodhi, S.N. Khan, F. Shaheen, M.I. Choudhary and Atta-ur-Rahman,Chem. Biodivers., 2, 487 (2005); https://doi.org/10.1002/cbdv.200590029.
F. D’Anna, F. Ferrante and R. Noto, Chem. Eur. J., 15, 13059 (2009); https://doi.org/10.1002/chem.200901788.
X. Han and D.W. Armstrong, Org. Lett., 7, 4205 (2005); https://doi.org/10.1021/ol051637w.
J.K.D. Surette, L. Green and R.D. Singer, Chem. Commun., 2753 (1996); https://doi.org/10.1039/CC9960002753.
V.R. Koch, L.L. Miller and R.A. Osteryoung, J. Am. Chem. Soc., 98, 5277 (1976); https://doi.org/10.1021/ja00433a037.
C.W. Lee, Tetrahedron Lett., 40, 2461 (1999); https://doi.org/10.1016/S0040-4039(99)00249-X.
A.L. Monteiro, F.K. Zinn, R.F. de Souza and J. Dupont, Tetrahedron Asymm., 8, 177 (1997); https://doi.org/10.1016/S0957-4166(96)00485-5.
K.S.A. Vallin, P. Emilsson, M. Larhed and A. Hallberg, J. Org. Chem., 67, 6243 (2002); https://doi.org/10.1021/jo025942w.
R.R. Deshmukh, R. Rajagopal and K.V. Srinivasan,Chem. Commun., 1544 (2001); https://doi.org/10.1039/b104532f.
R. Rajagopal, D.V. Jarikote and K.V. Srinivasan,Chem. Commun., 616 (2002); https://doi.org/10.1039/b111271f.
F. D’Anna, V. Frenna, V. Pace and R. Noto, Tetrahedron, 62, 1690 (2006); https://doi.org/10.1016/j.tet.2005.11.061.
J.L. Anderson, R. Ding, A. Ellern and D.W. Armstrong, J. Am. Chem. Soc., 127, 593 (2005); https://doi.org/10.1021/ja046521u.
T. Payagala, J. Huang, Z.S. Breitbach, P.S. Sharma and D.W. Armstrong, Chem. Mater., 19, 5848 (2007); https://doi.org/10.1021/cm702325a.
J.P.J. Marais, D. Ferreira and D. Slade, Phytochemistry, 66, 2145 (2005); https://doi.org/10.1016/j.phytochem.2005.03.006.
A. Urzhumtsev, E. von Castelmur and O. Mayans, Acta Cryst., 64, 478 (2008); https://doi.org/10.1107/S0907444908003442.
F. Micheli, F. Degiorgis, A. Feriani, A. Paio, A. Pozzan, P. Zarantonello and P. Seneci, J. Comb. Chem., 3, 224 (2001); https://doi.org/10.1021/cc0000949.
Y. Du, F. Tian and W. Zhao, Synth. Commun., 36, 1661 (2006); https://doi.org/10.1080/00397910600616602.
A.R. Katritzky, B.V. Rogovoy, C. Chassaing, V. Vvedensky, B. Forood, B. Flatt and H. Nakai, J. Heterocycl. Chem., 37, 1655 (2000); https://doi.org/10.1002/jhet.5570370642.
M. Yaeghoobi, H. Khaledi, Z. Abdullah and N.A. Rahman, ActaCryst., E67, o1693 (2011); https://doi.org/10.1107/S1600536811022112.