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[HSO3-pmim][CH3SO3] as an Efficient Catalyst for the Synthesis of 1,5-Benzodiazepine Derivatives under Ultrasound Irradiation
Corresponding Author(s) : Jing-Jun Ma
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
1,5-Benzodiazepine derivatives were synthesized in moderate to excellent isolated yields by the condensation reactions of o-phenylenediamine and ketones catalyzed by [1-methyl-3-(3-sulphopropyl)imidazolium methyl sulphate] under ultrasound irradiation using n-hexane as solvent. This method is simple, effective and gives better yields.
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- (a) H. Schutz, Benzodiazepines, Springer: Heidelberg (1982); (b) L.O. Randall and B. Kappel, In Benzodiazepines; Raven Press: New York (1973); (c) C.W. Kuo, S.V. More and C.F. Yao, Tetrahedron Lett., 47, 8523 (2006); (d) M. Essaber, A. Baouid, A. Hasnaoui, A. Benharref and J.P. Lavergne, Synth. Commun., 28, 4097 (1998); (e) A.M. El-Sayed, H. Abdel-Ghany and A.M.M. El-Saghier, Synth. Commun., 29, 3561 (1999); (f) J.X. Xu, H.T. Wu and S. Jin, Chin. J. Chem., 17, 84 (1999); (g) X.Y. Zhang, J.X. Xu and S. Jin, Chin. J. Chem., 17, 404 (1999); (h) K.V.V. Reddy, P.S. Rao and D. Ashok, Synth. Commun., 30, 1825 (2000).
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- (a) T. Welton, Chem. Rev., 99, 2071 (1999); (b) J. Dupont, R.F. de Souza and P.A.Z. Suarez, Chem. Rev., 102, 3667 (2002); (c) N. Jain, A. Kumar, S. Chauhan and S.M.S. Chauhan, Tetrahedron, 61, 1015 (2005); (d) S. Chowdhury, R.S. Mohan and J.L. Scott, Tetrahedron, 63, 2363 (2007).
- (a) S.G. Lee, Chem. Commun., 10, 1049 (2006); (b) B.C. Ranu and S. Banerjee, Org. Lett., 7, 3049 (2005); (c) A.L. Zhu, T. Jiang, D. Wang, B.X. Han, L. Liu, J. Huang, J.C. Zhang and D.H. Sun, Green Chem., 7, 514 (2005).
- (a) J.J. Ma, X. Zhou, X.H. Zang, C. Wang, Z. Wang, J.C. Li and Q. Li, Aus. J. Chem., 60, 146 (2007); (b) J.J. Ma, S.T. Gao, Z. Li, R.X. Tang, H.Y. Liu, C. Wang and Y. Gao, Chin. J. Org. Chem., 28, 339 (2008); (c) J.J. Ma, X.H. Zang, X. Zhou, C. Wang, J.C. Li and Q. Li, Indian J. Chem. Sec., 46B, 2045 (2007); (d) C. Wang, J.J. Ma, X. Zhou, X. H. Zang, Z. Wang, Y. J.Gao and P.L. Cui, Synth. Commun., 35, 2759 (2005).
- L. Zhang, M. Xian, Y.C. He, L.Z. Li, J.M. Yang, S.T. Yu and X. Xu, Bioresour. Technol., 100, 4368 (2009).
- W.B. Yi and C. Cai, Synth. Commun., 37, 3827 (2007).
- J.S. Yadav, B.V.S. Reddy, S. Praveenkumar, K. Nagaiah, N. Lingaiah and P.S. Saiprasad, Synthesis, 901 (2004)
References
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(a) S.K. De and R.A. Gibbs, Tetrahedron Lett., 46, 1811 (2005); (b) P. Stahlhofen and W. Ried, Chem. Ber., 90, 815 (1957); (c) J.A.L. Herbert and H. Suschitzky, J. Chem. Soc., Perkin Trans. I, 2657 (1974); (d) H.R. Morales, A. Bulbarela and R. Contreras, Heterocycles, 24, 135 (1986); (e) D.I. Jung, T.W. Choi, Y.Y. Kim, I.S. Kim, Y.M. Park, Y.G. Lee and D.H. Jung, Synth. Commun., 29, 1941 (1999); (f) R. Varala, R. Enugala, S. Nuvula and S.R. Adapa, Synlett, 1009 (2006); (g) M.S. Balakrishna and B. Kaboudin, Tetrahedron Lett., 42, 1127 (2001); (h) M. Curini, F. Epifano, M.C. Marcotullio and O. Rosati, Tetrahedron Lett., 42, 3193 (2001); (i) B. Kaboudin and K. Navaee, Heterocycles, 55, 1443 (2001); (j) M. Pozarentzi, J.S. Stephanatou and C.A. Tsoleridis, Tetrahedron Lett., 43, 1755 (2002); (k) J.S. Yadav, B.V.S. Reddy, B. Eshwaraiah and K. Anuradha, Green Chem., 4, 592 (2002); (l) G. Sabitha, G.S.K.K. Reddy, K.B. Reddy, N.M. Reddy and J.S. Yadav, Adv. Synth. Catal., 346, 921 (2004); (m) J.S. Yadav, B.V.S. Reddy, S.P. Kumar and K. Nagaiah, Synthesis, 480 (2005).
(a) G. Cravotto and P. Cintas, Chem. Soc., 35, 180 (2006); (b) J.Y. He, H.X. Xin, H. Yan, X.Q. Song and R.G. Zhong, Ultrason. Sonochem., 18, 466 (2011); (c) S.H. Gou, H.C. Chen, Z.P. Fang, J. Luo and Y.L. Wang, Chin. J. Org. Chem., 24, 234 (2004); (d) T.J. Mason and J.P. Lorimer, Applied Sonochemistry: The Uses of Power Ultrasound in Chemistry and Processing, Wiley-VCH, Weinheim (2002); (e) S.M. Zhang, H. Li, X.C. Zheng, B.Q. Li, S.H. Wu, W.P. Huang, Z.G. Liu and Y. Feng, Chin. J. Org. Chem., 22, 603 (2002); (f) G.V. Ambulgekar, B.M. Bhanage and S.D. Samant, Tetrahedron Lett., 46, 2483 (2005); (g) J.T. Li, T.S. Li, L.J. Li and X. Cheng, Ultrason. Sonochem., 6, 199 (1999).
(a) T. Welton, Chem. Rev., 99, 2071 (1999); (b) J. Dupont, R.F. de Souza and P.A.Z. Suarez, Chem. Rev., 102, 3667 (2002); (c) N. Jain, A. Kumar, S. Chauhan and S.M.S. Chauhan, Tetrahedron, 61, 1015 (2005); (d) S. Chowdhury, R.S. Mohan and J.L. Scott, Tetrahedron, 63, 2363 (2007).
(a) S.G. Lee, Chem. Commun., 10, 1049 (2006); (b) B.C. Ranu and S. Banerjee, Org. Lett., 7, 3049 (2005); (c) A.L. Zhu, T. Jiang, D. Wang, B.X. Han, L. Liu, J. Huang, J.C. Zhang and D.H. Sun, Green Chem., 7, 514 (2005).
(a) J.J. Ma, X. Zhou, X.H. Zang, C. Wang, Z. Wang, J.C. Li and Q. Li, Aus. J. Chem., 60, 146 (2007); (b) J.J. Ma, S.T. Gao, Z. Li, R.X. Tang, H.Y. Liu, C. Wang and Y. Gao, Chin. J. Org. Chem., 28, 339 (2008); (c) J.J. Ma, X.H. Zang, X. Zhou, C. Wang, J.C. Li and Q. Li, Indian J. Chem. Sec., 46B, 2045 (2007); (d) C. Wang, J.J. Ma, X. Zhou, X. H. Zang, Z. Wang, Y. J.Gao and P.L. Cui, Synth. Commun., 35, 2759 (2005).
L. Zhang, M. Xian, Y.C. He, L.Z. Li, J.M. Yang, S.T. Yu and X. Xu, Bioresour. Technol., 100, 4368 (2009).
W.B. Yi and C. Cai, Synth. Commun., 37, 3827 (2007).
J.S. Yadav, B.V.S. Reddy, S. Praveenkumar, K. Nagaiah, N. Lingaiah and P.S. Saiprasad, Synthesis, 901 (2004)