Metal-Organic Framework Zn3(BTC)2: As Recyclable and heterogeneous Catalyst for the Synthesis of 1,5-Benzodiazepine Compounds

Document Type : Original Article

Authors

1 Department of Chemistry, Payame Noor University, PO BOX 19395-4697, Iran, tehran

2 Department of chemistry, Payame Noor University, Tehran

3 pnu university

Abstract

In this work, with a simple and mild method, 1,5-benzodiazepine compounds were synthesized using the condensation of o-phenylenediamine derivatives and liner and cyclic ketones in the presence of the metal-organic framework Zn3(BTC)2 in ethanol at 50 °C. All products with excellent yields (86-94%) were obtained. Nanoparticles Zn3(BTC)2 have the advantages such as non-toxic, stable in solvents and harsh conditions, easy synthesis, high activity, easy separation from the reaction mixture by filtering and recyclable without losing its activity.
In this work, with a simple and mild method, 1,5-benzodiazepine compounds were synthesized using the condensation of o-phenylenediamine derivatives and liner and cyclic ketones in the presence of the metal-organic framework Zn3(BTC)2 in ethanol at 50 °C. All products with excellent yields (86-94%) were obtained. Nanoparticles Zn3(BTC)2 have the advantages such as non-toxic, stable in solvents and harsh conditions, easy synthesis, high activity, easy separation from the reaction mixture by filtering and recyclable without losing its activity.

Keywords

Main Subjects

References

[1] V. R. Jumde, E. Cini, A. Porcheddu, M. Taddei, European Journal of Organic Chemistry, 2015 (2015)1068. 
[2] L. -Z. Wang, X. -Q. Li, Y.-S. An, Organic & Biomolecular Chemistry, 13 (2015)5497.
[3] Y. Huang, K. Khoury, T. Chanas, A. Dömling, Organic Letters, 14 (2012)5916.
[4] D.V. Jarikote, S.A. Siddiqui, R. Rajagopal, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Tetrahedron Letters, 44(2003)1835.
[5] M. Pozarentzi, J. Stephanidou-Stephanatou, C.A. Tsoleridis, Tetrahedron Letters, 43 (2002)1755.
[6] J.N. Sangshetti, N.D. Kokare, D.B. Shinde, Chinese Chemical Letters, 18 (2007)1305.
[7] X. Zhou, M.Y. Zhang, S.T. Gao, J.J. Ma, C. Wang, C. Liu, Chinese Chemical Letters, 20 (2009)905.
[8] G.K.S. Prakash, F. Paknia, A. Narayan, T. Mathew, G.A. Olah, Journal of Fluorine Chemistry, 152 (2013)99.
[9] M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, Tetrahedron Letters, 42 (2001)3192.
[10] K. De, R.A. Gibbs, Tetrahedron Letters, 46 (2005)1811.
[11] S. Sajjadifar, S. Rezayati, International Journal of ChemTech Research, 5 (2013)1964.
[12] R. X. Shi, Y. K. Liu, Z. Y. Xu, Journal of Zhejiang University SCIENCE B,  11 (2010)102.
[13] D. V. Jarikote, S. A. Siddiqui, R. Rajagopal, D. Thomas, R. J. Lahoti, K. V. Srinivasan, Tetrahedron Letters,  44 (2003)1835.
[14] V.V.K.M. Kandepi, N. Narender, Catalysis Science & Technology, 2 (2012)471.
[15] A. B. Mirza, H. Kh. Rahim, Z. Solmaz, J. Of Applied Chemistry, 10 (1394) 61, in Persian.
[16] D.J. Tranchemontagne, M.O.k. Ni, O.M. Yaghi, Angewandte Chemie International Edition, 47 (2008)5136.
[17] Z.-Q. Li, L.-G. Qiu, T. Xu, Y. Wu, W. Wang, Z.-Y. Wu, X. Jiang, Materials Letters, 63 (2009) 78.
[18] B. Chen, S. Xiang, G. Qian, Accounts of Chemical Research, 43 (2010)1115.
[19] Z.-Y. Gu, J. Park, A. Raiff, Z. Wei, H.-C. Zhou, ChemCatChem, 6 (2014)67.
[20] S. Zahra, R. Mahmoud, A. Ahmad, M. B. Tahereh, J. Of Applied Chemistry, 46 (1397) 29, in Persian.
[21] A. Dhakshinamoorthy, M. Alvaro, A. Corma, H. Garcia, Dalton Transactions, 40 (2011)634.
[22] L. T. L. Nguyen, C. V. Nguyen, GH. Dang, KKA. Le, NTS. Phan, Journal of Molecular Catalysis A: Chemical, 349 (2011)28.
[23] A. Dhakshinamoorthy, M. Alvaro, H. Garcia, ACS Catalysis, 1 (2011) 48.
[24] F. Song, C. Wang, J. M. Falkowski, L. Ma, W. Lin, Journal of the American Chemical Society, 152 (2011)15390.
[25] F. Xamena, A. Abad, A. Corma, H. Garcia, Journal of Catalysis, 250 (2007)294.
[26] S. Gao, N. Zhao, M. Shu, S. Che, Applied Catalysis A: General, 388 (2010)196.
[27] Y. Zhou, J. Song, S. Liang, S. Hu, H. Liu, T. Jiang, B. Han, Journal of Molecular Catalysis A: Chemical,  308 (2009)68.
[28] S. Neogi, M. K. Sharma, P. K. Bharadwaj, Journal of Molecular Catalysis A: Chemical, 299 (2009)1.
[29] K. K. Tanabe, S. M. Cohen, Inorganic Chemistry, 49 (2010)6766.
[30] S. Sajjadifar, Z. Arzehgar, S. Khoshpoori, J. Inorg. Organomet. Polym. Mate. (2017)1-10.S.
[31] S. Sajjadifar, Z. Arzehgar, A. Ghayuri, J. Chin. Chem. Soc., 65(2017)205.
[32] K. Reddy, Ch.Reddy, M. Mahesh, K. Reddy, P. V. K. Raju, V. V. Reddy, Can. J. Chem., 85(2007)184.
[33] S. V. Goswami, P. B. Thorat, S. R.Bhusare, J. Chem. Sci. 125(2013)745.
[34] B. Das, M. R. Reddy, R. Ramu, K. R. Reddy, M. Geethangili, J. Chem. Res., 9(2005)598.
[34] A. Maleki, N. Ghamari, M. Kamalzare, RSC Adv., 4(2014) 9416.
Applied Chemistry Today
Volume 14, Issue 51
July 2019
Pages 213-222

Files

Share

How to cite

Statistics