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Synthesis of 1,5-Benzodiazepine Derivatives Using p-Toluenesulfonic Acid as Catalyst
Asian Journal of Chemistry,
Vol. 27 No. 2 (2015): Vol 27 Issue 2
Abstract
A series of substituted ethyl 4-oxo-4-phenylbut-2-enoates were prepared and reacted with substituted o-phenylenediamine, undergone Michael addition reactions and cyclodehydration to provide novel 4-phenyl-2,3-dihydro-1,5-benzodiazepine-2- carboxylate derivatives with excellent yields. The synthetic protocol fulfilled many green-chemical requirements by using simple catalyst p-toluenesulfonic acid as activator and ethanol as solvent at room temperature.
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- J.K. Landquist, eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry, Pergamon, Oxford, Vol. 1, pp. 166-170 (1984).
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- J.A.L. Herbert and H.J. Suschitzky, Chem. Soc. Perkin Trans. I, 2657 (1974); doi:10.1039/p19740002657.
- R. Contreras, H. R. Morales and A. Bulbarela, Heterocycles, 24, 135 (1986); doi:10.3987/R-1986-01-0135.
- M.S. Balakrishna and B. Kaboudin, Tetrahedron Lett., 42, 1127 (2001); doi:10.1016/S0040-4039(00)02168-7.
- B. Kaboudin and K. Navaee, Heterocycles, 55, 1443 (2001); doi:10.3987/COM-01-9253.
- M. Pozarentzi, J. Stephanidou-Stephanatou and C.A. Tsoleridis, Tetrahedron Lett., 43, 1755 (2002); doi:10.1016/S0040-4039(02)00115-6.
- M. Curini, F. Epifano, M.C. Marcotullio and O. Rosati, Tetrahedron Lett., 42, 3193 (2001); doi:10.1016/S0040-4039(01)00413-0.
- L.F. Xiao, C.G. Xia and J. Chen, Tetrahedron Lett., 48, 7218 (2007); doi:10.1016/j.tetlet.2007.07.171.
- T. Li, Y. Souma and Q. Xu, Catal. Today, 111, 288 (2006); doi:10.1016/j.cattod.2005.10.038.
- L.Z. Wang, Z.x. Hua and S.S. Wang, Chinese J. Org. (In press).
References
J.K. Landquist, eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry, Pergamon, Oxford, Vol. 1, pp. 166-170 (1984).
H. Schutz, Benzodiazepines. Springer, Heidelberg (1982).
M. Di Braccio, G. Grossi, G. Roma, L. Vargiu, M. Mura and M.E. Marongiu, Eur. J. Med. Chem., 36, 935 (2001); doi:10.1016/S0223-5234(01)01283-1.
G. Semple, H. Ryder, D.A. Kendrick, M. Szelke, M. Ohta, M. Satoh, A. Nishida, S. Akuzawa and K. Miyata, Bioorg. Med. Chem. Lett., 6, 55 (1996); doi:10.1016/0960-894X(95)00557-A.
T. Hussenether, H. Hübner, P. Gmeiner and R. Troschütz, Bioorg. Med. Chem. Lett., 12, 2625 (2004); doi:10.1016/j.bmc.2004.03.023.
(a) J. Knabe, H.P. Büch and S. Bender, Arch. Pharm., 328, 59 (1995); doi:10.1002/ardp.19953280111; (b) R.N. Brogden, R.C. Heel, T.M. Speight and G.S. Avery, Drugs, 20, 161 (1980); doi:10.2165/00003495-198020030-00001.
(a) K.S. Atwal, J.L. Bergey, A. Hedberg and S. Moreland, J. Med. Chem., 30, 635 (1987); doi:10.1021/jm00387a009; (b) Z. Khabnadideh, Z. Rezaei, A. Khalafi-Nezhad, R. Bahrinajafi, R. Mohamadi and A.A. Farrokhroz, Bioorg. Med. Chem. Lett., 13, 2863 (2003); doi:10.1016/S0960-894X(03)00591-2.
M. Di Braccio, G. Grossi, G. Roma, L. Vargiu, M. Mura and M.E. Marongiu, Eur. J. Med. Chem., 36, 935 (2001); doi:10.1016/S0223-5234(01)01283-1.
A. Chimirri, S. Grasso, R. Ottanà, G. Romeo and M. Zappalà, J. Heterocycl. Chem., 27, 371 (1990); doi:10.1002/jhet.5570270250.
X.Q. Pan, J.P. Zou, Z. Huang and W. Zhang, Tetrahedron Lett., 49, 5302 (2008); doi:10.1016/j.tetlet.2008.06.082.
J.A.L. Herbert and H.J. Suschitzky, Chem. Soc. Perkin Trans. I, 2657 (1974); doi:10.1039/p19740002657.
R. Contreras, H. R. Morales and A. Bulbarela, Heterocycles, 24, 135 (1986); doi:10.3987/R-1986-01-0135.
M.S. Balakrishna and B. Kaboudin, Tetrahedron Lett., 42, 1127 (2001); doi:10.1016/S0040-4039(00)02168-7.
B. Kaboudin and K. Navaee, Heterocycles, 55, 1443 (2001); doi:10.3987/COM-01-9253.
M. Pozarentzi, J. Stephanidou-Stephanatou and C.A. Tsoleridis, Tetrahedron Lett., 43, 1755 (2002); doi:10.1016/S0040-4039(02)00115-6.
M. Curini, F. Epifano, M.C. Marcotullio and O. Rosati, Tetrahedron Lett., 42, 3193 (2001); doi:10.1016/S0040-4039(01)00413-0.
L.F. Xiao, C.G. Xia and J. Chen, Tetrahedron Lett., 48, 7218 (2007); doi:10.1016/j.tetlet.2007.07.171.
T. Li, Y. Souma and Q. Xu, Catal. Today, 111, 288 (2006); doi:10.1016/j.cattod.2005.10.038.
L.Z. Wang, Z.x. Hua and S.S. Wang, Chinese J. Org. (In press).