Synthesis, characterization and catalytic application of Fe3O4@Cys–SO3H for preparation of 2H-indazolo[1,2-b]phthalazine-triones
محورهای موضوعی : Iranian Journal of Catalysis
Somaye Nikzad Shalkouhi
1
(Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran.)
Hassan Kefayati
2
(Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran.)
Shahab Shariati
3
(Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran.)
کلید واژه: Fe3O4, L-cysteine, 2H-indazolo [1, 2-b] phthalazine-triones, Fe3O4@Cys&ndash, SO3H,
چکیده مقاله :
The surface ofFe3O4 magnetic nanoparticles (MNPs) was modified by L-cysteine through condensation of COOH groups of L-cysteine and OH groups on the surface of Fe3O4. The –SH group of preparedFe3O4@Cys MNPs oxidized to –SO3H group and Fe3O4@Cys–SO3H as an environmentally friendly magnetic nanoparticle was prepared. The MNPs were characterized by FT-IR, XRD, SEM and TEM studies. Then, the catalytic activity of the MNPs was evaluated as an effective and reusable catalyst for one-pot synthesis of 2H‐indazolo [1,2‐b] phthalazine‐triones derivatives. The results show that the catalytic activity of Fe3O4@Cys–SO3H was comparable to that of other reported heterogeneous and homogeneous catalysts.
[1] X.F. Shen, Q. Wang, W.L. Chen, Y.H. Pang, Appl. Surf. Sci. 317 (2014) 1028–1034.
[2] (a) M. Arruebo, R. Fernandez-Pacheco, M.R. Ibarra, J. Santamaria, J. Pharm. Sci. 97 (2008) 2948–2983.
[3] (a) Y.Y. Xu, M. Zhou, H.J. Geng, J.J. Hao, Q.Q. Ou, S.D. Qi, H.L. Chen, X.G. Chen, Appl. Surf. Sci. 258 (2012) 3897-3902. (b) Y.R. Zhang, S.Q. Wang, S.L. Shen, B.X. Zhao, Chem. Eng. J. 233 (2013) 258-264. (c) D.P. Li, Y.R. Zhang, X. Zhao, B.X. Zhao, Chem. Eng. J. 232 (2013) 425-433.
[4] T. Zeng, W.W. Chen, C.M. Cirtiu, A. Moores, G. Song, C.J. Li, Green Chem. 12 (2010) 570–573.
[5] (a) L. Vayssières , C. Chanéac, E. Tronc, J.P. Jolivet J. Colloid Interface Sci. 205 (1998) 205–212. (b) R.Y. Hong, B. Feng, G. Liu, S. Wang, H.Z. Li, J. Alloy Compd. 476 (2009) 612-618.
[6] (a) Y.R. Zhang, P. Su, J. Huang, Q.R. Wang, B.X. Zhao, Chem. Eng. J. 262 (2015) 313-318. (b) F. Ge, H. Ye, M.M. Li, X. Zhao, Chem. Eng. J. 198 (2012) 11-17. (c) S.H. Araghi, M.H. Entezari, Appl. Surf. Sci. 333 (2015) 68-77.
[7] J. Safari, L. Javadian, Ultrason Sonochem. 22 (2015) 341-348.
[8] X.Y. Zou, Y.B. Yin, Y.B. Zhao, D.Y. Chen, S. Dong, Mater Lett. 150 (2015) 59-61.
[9] H.L. Fan, L. Li, S.F. Zhou, Y.Z. Liu, Ceram. Int. 42 (2016) 4228-4237.
[10] X. Shen, Q. Wang, W.L. Chen, Y. Pang, Appl. Surf. Sci. 317 (2014) 1028-1034.
[11] J. Mondal, T. Sen, A. Bhaumik, Dalton Trans. 41 (2012) 6173-6181.
[12] M.B. Gawande, P.S. Branco, A. Velhinho, I.D. Nogueira, RSC Adv. 2 (2012) 6144-6149.
[13] (a) R.W. Carling, K.W. Moore, L.J. Street, D. Wild, C. Isted, P.D. Leeson, S. Thomas, D. O'Connor, R.M. McKernan, K. Quirk, S.M. Cook, J.R. Atack, K.A. Wafford, S.A. Thompson, G.R. Dawson, P. Ferris, J.L. Castro, J. Med. Chem. 47 (2004) 1807-1822. (b) R.P. Jain, J.C. Vederas, Bioorg. Med. Chem. Lett. 14 (2004) 3655-3658.
[14] (a) S. Grasso, G.D. Sarro, A.D. Sarro, N. Micale, M. Zappala, G. Puja, M. Baraldi, C.D. Micheli, J. Med. Chem. 43 (2000) 2851-2859. (b) L. Zhang, L.P. Guan, X.Y. Sun, C.X. Wei, K.Y. Chai, Z.S. Quan, Chem. Biol. Drug. Des. 73 (2009) 313-319.
[15] Y. Nomoto, H. Obase, H. Takai, M. Teranishi, J. Nakamura, K. Kubo, Chem. Pharm. Bull. 38 (1990) 2179-2183.
[16] N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama, H. Adachi, J. Med. Chem. 41 (1998) 3367-3372.
[17] J. Li, Y. Zhao, X. Yuan, J. Xu, P. Gong, Molecules 11 (2006) 574-582.
[18] C.K. Ryu, R.E. Park, M.Y. Ma, J.H. Nho, Bioorg. Med. Chem. Lett. 17 (2007) 2577-2580.
[19] S.S. El-Saka, A.H. Soliman, A.M. Imam, Afinidad 66 (2009) 167-172.
[20] J. Sinkkonen, V. Ovcharenko, K.N. Zelenin, I.P. Bezhan, B.A. Chakchir, F. Al-Assar, K. Pihlaja, Eur. J. Org. Chem. (2002) 2046-2053.
[21] M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron 64 (2008) 2375-2378.
[22] R. Fazaeli, H. Aliyan, N. Fazaeli, Open Catal. J. 3 (2010) 14-18.
[23] G. Shukla, R.K. Verma, G.K. Verma, M.S. Singh, Tetrahedron Lett. 52 (2011) 7195‐7198.
[24] Sh. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, Tetrahedron Lett. 50 (2009) 7300-7303.
[25] H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A 345 (2008) 128-133.
[26] A. Varghese, A. Nizam, R. Kulkarn, L. George, Eur. J. Chem. 4 (2013) 132-135.
[27] E. Mosaddegh, A. Hassankhani, Tetrahedron Lett. 52 (2011) 488-490.
[28] G. Sabitha, C. Srinivas, A. Raghavendar, J.S. Yadav, Helv. Chim. 93 (2010) 1375.
[29] R.G. Vaghei, R.K. Nami, Z.T. Semiromi, M. Amiri, Tetrahedron 67 (2011) 1930.
[30] S. Gaurav, K.V. Rajiv, K.V. Girijesh, S. Shankar, M. Singh, Tetrahedron Lett. 52 (2011) 7195-7198.
[31] W. Xiao, M.W. Wei, W.L. Qiang, Y.F. Lin, J. Chin. Chem. Soc. 57 (2010) 1341-1345.
[32] W.H. Juan, Z.X. Nan, Z.Z. Hui, Monatsh. Chem. 141 (2010) 425-430.
[33] (a) N. Saadatjoo, M. Golshekan, Sh. Shariati, H. Kefayati, P. Azizi, J. Mol. Catal. A: Chem. 377 (2013) 173-179. (b) H. Kefayati, M. Golshekan, Sh. Shariati, M. Bagheri, Chin. J. Catal. 36 (2015) 572-578.
[34] (a) H. Kefayati, S. Jirsaray-Bazargard, P. Vejdansefat, Sh. Shariati, A. Mehtar Kohankar, Dyes Pigm. 125 (2016) 309-315. (b) H. Kefayati, A. Mehtar Kohankar, N. Ramzanzadeh, Sh. Shariati, S. Jirsaray-Bazargard, J. Mol. Liq. 209 (2015) 617-624.
[35] L. Zhang, R. He, H.-C. Gu, Appl. Surf. Sci. 253 (2006) 2611-2617.
[36] J.H. Jang, H.B. Lim, Microchem. J. 94 (2010) 148-158.
[37] R. Tayebee, M.M. Aminib, S. Pouyamanesha, A. Aliakbari, Dalton Trans. 44 (2015) 9596-9609.
