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Copyright (c) 2014 Yuhao Zhao1, Xuejie Yu2, Manpreet Saini3, Yanxu Ma4, Rajesh K. Singh3
This work is licensed under a Creative Commons Attribution 4.0 International License.
Highly Efficient Zinc Oxide Nanoparticles Catalyzed Green Synthesis of 1,5-Benzodiazepines under Solvent-Free Path
Corresponding Author(s) : Yuhao Zhao1
Asian Journal of Chemistry,
Vol. 26 No. 24 (2014)
Abstract
An efficient and simple environment-friendly method for the preparation of substituted 1,5-benzodiazepines as biologically interesting compounds under heterogenous catalyst is described. The one-pot multicomponent condensation of o-phenylene-diamine and substituted ketones catalyzed by zinc oxide nanoparticles (ZnO NPs) under microwave under solvent-free condition has been developed. The present protocol provides a green and improved pathway for the synthesis of 1,5-benzodiazepines in terms of excellent yields, short reaction times and reusability of catalyst.
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- I. Ugi, Pure Appl. Chem., 73, 187 (2011).
- D.J. Ramon and M. Yus, Angew. Chem. Int. Ed., 44, 1602 (2005).
- L.O. Randall and B. Kappel, in eds.: S. Garattini, E. Mussini and L.O. Randall, Benzodiazepines, Raven Press: New York, p. 27 (1973).
- H. Schutz, Benzodiazepines, Springer: Heidelberg (1982).
- L.K. Landquist, Comprehensive Heterocyclic Chemistry, Pergamon: Oxford, vol. 1, p. 166 (1984).
- R. Varala, R. Enugala and S.R. Adapa, J. Braz. Chem. Soc., 18, 291 (2007).
- A.M. El-Sayed, A. Khodairy, H. Salah and H. Abdel-Ghany, Phosphorous Sulphur Silicon Rel. Elem., 182, 711 (2007).
- X.-Q. Li and L.-Z. Wang, Chin. Chem. Lett., 25, 327 (2014).
- S.S. Ilango, P.U. Remya and S. Ponnuswamy, Ind. J. Chem., 52B, 136 (2013).
- J.H. Clark, Pure Appl. Chem., 73, 103 (2001).
- H.H. Kung, Transition Metal Oxides: Surface Chemistry and Catalysis, Elsevier Science, New York, NY, USA, (1989).
- C. Pacholski, A. Kornowski and H. Weller, Angew. Chem., 41, 1188 (2002).
- F.M. Moghaddam, H. Saeidian, Z. Mirjafary and A. Sadeghi, J. Iranian Chem. Soc., 6, 317 (2009).
- B.V. Kumar, H.S.B. Naik, D. Girija and B.V. Kumar, J. Chem. Sci., 123, 615 (2011).
- M. Hosseini-Sarvari, J. Iranian Chem. Soc., 8(S1), S119 (2011).
- I. Yavari and S. Beheshti, J. Iranian Chem. Soc., 8, 1030 (2011).
- J. Safaei-Ghomi, M.A. Ghasemzadeh and S. Zahedi, J. Mex. Chem. Soc., 57, 1 (2013).
- (a) R. Duvedi and R.K. Singh, Asian J. Chem., 24, 5665 (2012); (b) A. Sandhar, D.N. Prasad and R.K. Singh, Indian J. Heterocycl. Chem., 21, 369 (2012); (c) A. Sandhar, D.N. Prasad, A. Kapoor and R.K. Singh, Curr. Res. Chem., 4, 68 (2012).; (d) A. Sandhar and R.K. Singh, Asian J. Chem., 24, 5643 (2012); (e) S. Malik, S. Sharma and R.K. Singh, Asian J. Chem., 24, 5669 (2012); (f) P. Kaur, H. Sharma, R. Rana, D.N. Prasad and R.K. Singh, Asian J. Chem., 24, 5649 (2012); (g) Y. Zhao, S. Sharma, M. Huang, A. Kaur, R.K. Singh and Y. Ma, Asian J. Chem., 26, 5116 (2014); (h) T. Li, X. Zhai, D. Singh, R.K. Singh and X. Xu, Asian J. Chem., 26, 5207 (2014).
- J. Safaei-Ghomi and M.A. Ghasemzadeh, Arab. J. Chem., doi:10.1016/j.arabjc.2013.06.030.
References
I. Ugi, Pure Appl. Chem., 73, 187 (2011).
D.J. Ramon and M. Yus, Angew. Chem. Int. Ed., 44, 1602 (2005).
L.O. Randall and B. Kappel, in eds.: S. Garattini, E. Mussini and L.O. Randall, Benzodiazepines, Raven Press: New York, p. 27 (1973).
H. Schutz, Benzodiazepines, Springer: Heidelberg (1982).
L.K. Landquist, Comprehensive Heterocyclic Chemistry, Pergamon: Oxford, vol. 1, p. 166 (1984).
R. Varala, R. Enugala and S.R. Adapa, J. Braz. Chem. Soc., 18, 291 (2007).
A.M. El-Sayed, A. Khodairy, H. Salah and H. Abdel-Ghany, Phosphorous Sulphur Silicon Rel. Elem., 182, 711 (2007).
X.-Q. Li and L.-Z. Wang, Chin. Chem. Lett., 25, 327 (2014).
S.S. Ilango, P.U. Remya and S. Ponnuswamy, Ind. J. Chem., 52B, 136 (2013).
J.H. Clark, Pure Appl. Chem., 73, 103 (2001).
H.H. Kung, Transition Metal Oxides: Surface Chemistry and Catalysis, Elsevier Science, New York, NY, USA, (1989).
C. Pacholski, A. Kornowski and H. Weller, Angew. Chem., 41, 1188 (2002).
F.M. Moghaddam, H. Saeidian, Z. Mirjafary and A. Sadeghi, J. Iranian Chem. Soc., 6, 317 (2009).
B.V. Kumar, H.S.B. Naik, D. Girija and B.V. Kumar, J. Chem. Sci., 123, 615 (2011).
M. Hosseini-Sarvari, J. Iranian Chem. Soc., 8(S1), S119 (2011).
I. Yavari and S. Beheshti, J. Iranian Chem. Soc., 8, 1030 (2011).
J. Safaei-Ghomi, M.A. Ghasemzadeh and S. Zahedi, J. Mex. Chem. Soc., 57, 1 (2013).
(a) R. Duvedi and R.K. Singh, Asian J. Chem., 24, 5665 (2012); (b) A. Sandhar, D.N. Prasad and R.K. Singh, Indian J. Heterocycl. Chem., 21, 369 (2012); (c) A. Sandhar, D.N. Prasad, A. Kapoor and R.K. Singh, Curr. Res. Chem., 4, 68 (2012).; (d) A. Sandhar and R.K. Singh, Asian J. Chem., 24, 5643 (2012); (e) S. Malik, S. Sharma and R.K. Singh, Asian J. Chem., 24, 5669 (2012); (f) P. Kaur, H. Sharma, R. Rana, D.N. Prasad and R.K. Singh, Asian J. Chem., 24, 5649 (2012); (g) Y. Zhao, S. Sharma, M. Huang, A. Kaur, R.K. Singh and Y. Ma, Asian J. Chem., 26, 5116 (2014); (h) T. Li, X. Zhai, D. Singh, R.K. Singh and X. Xu, Asian J. Chem., 26, 5207 (2014).
J. Safaei-Ghomi and M.A. Ghasemzadeh, Arab. J. Chem., doi:10.1016/j.arabjc.2013.06.030.