Synthesis of spirooxindole derivatives catalyzed by Fe (III)@graphitic carbon nitride nanocomposite via one-pot multi-component reaction

Document Type: Articles

Authors

1 Department of Chemistry, Faculty of Science, University of Birjand, P. O. Box 97175-615, Birjand, Iran.

2 Department of Chemistry, Faculty of Science, University of Birjand, P. O. Box 97175-615, Birjand, Iran

Abstract

Fe (III) supported graphitic carbon nitride nanocomposite was synthesized by impregnation of FeCl3 with g- C3N4 (Fe (III)@g-C3N4). Then, the synthesis of spirooxindole derivatives was carried out in the presence of Fe (III) @ graphitic carbon nitride nanocompositevia the multi-component reaction of malononitrile, isatins, and 1,3-dicarbonyl compounds in green media (ethanol/water (1:1)) under reflux conditions and the corresponding products were prepared in good to excellent yields (70-98 %). Also, the heterogeneous nanocatalyst was characterized by different techniques including the transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), thermal gravimetric analysis (TGA), atomic absorption spectroscopy (AAS) and X-ray diffraction (XRD). Furthermore, the nanocomposite is recoverable and reusable several times without a negligible decrease in its catalytic performance.

Keywords


[1] J. Cao, S. Shen, P. Yang, J. Qu, A, Org. Lett. 15 (2013) 3856-3859.
[2] P. Zhang, T. Wu, T. Jiang, W. Wang, H. Liu, H. Fan, Z. Zhang, B. Han, Green Chem. 15 (2013) 152-159.
[3] T. Wu, P. Zhang, T. Jiang, D. Yang, B. Han, Sci. China Chem. 58 (2015) 93-100.
[4] H. Liu, T. Jiang, B. Han, S. Liang, W. Wang, T. Wu, G. Yang, Green Chem. 13 (2011) 1106-1109.
[5] Y.H. Choa, J.K. Yang, B.H. Kim, Y.K. Jeong, J.S. Lee, T. Nakayama, J. Magn. Magn. Mater. 266 (2003) 12-19.
[6] P.H.C. Camargo, K.G. Satyanarayan, F. Wypych, Mater. Res. 12 (2009) 1-39.
[7] P. Zapata, R. Quijada, J. Retuert, E. Moncada, J. Chil. Chem. Soc. 53 (2008) 1369-1371.
[8] P. Zhang, Y. Wang, J. Yao, C. Wang, C. Yan, M. Antonietti, H. Li, Adv. Synth. Catal. 353 (2011) 1447-1451.
[9] F.Z. Su, S. Mathew, G. Lipner, X.Z. Fu, M. Antonietti, S. Blechert, X.C. Wang, J. Am. Chem. Soc. 132 (2010) 16299-16301.
[10] F.Z. Su, S. Mathew, L. Molmann, M. Antonietti, X.C. Wang, S. Blechert, Angew. Chem. Int. Ed. 50 (2011) 683-686.
[11] Y. Wang, X. Wang, M. Antonietti, Angew. Chem. Int Ed. 51 (2012) 68-89.
[12] Y. Gong, M. Li, H. Li, Y. Wang, Green Chem. 17 (2015) 715-736.
[13] Y. Wang, H. Li, J. Yao, X. Wang, M. Antonietti, Chem. Sci. 2 (2011) 446-450.
[14] X. Miao, X. Shen, J. Wu, Z. Ji, J. Wang, L. Kong, M. Liu, C. Song, Appl. Catal. A 539 (2017) 104-113.
[15] H. Liu, Z. Xu, Z. Zhang, D. Ao, Appl. Catal. A 518 (2016) 150-157.
[16] L. Ge, C. Han, J. Liu, Y. Li, Appl. Catal. A 409-410 (2011) 215-222.
[17] Q. Hao, X. Niu, C. Nie, S. Hao, W. Zou, J. Gea, D. Chen, W. Yao, Phys. Chem. Chem. Phys.18 (2016) 31410-31418.
[18] B. Lin, C. Xue, X. Yan, G. Yang, G. Yang, B. Yang, Appl. Surf. Sci. 357 (2015) 346-355.
[19] H.-B. Fang, Y. Luo, Y.-Z. Zheng, W. Ma, X. Tao, Ind. Eng. Chem. Res. 55 (2016) 4506-4514.
[20] S.C. Yan, Z.S. Li, Z.G. Zou, Langmuir 25 (2009) 10397-10401.
[21] T. Fukuyama, X. Chen, J. Am. Chem. Soc. 116 (1994) 3125-3126.
[22] T.L. Pavlovska, R.G. Redkin, V.V. Lipson, D.V. Atamanuk, Mol. Diversity 20 (2016) 299-344.
[23] A. Allahresani, M.A. Nasseri, RSC Adv. 4 (2014) 60702-60710.
[24] A. Allahresani, M.A. Nasseri, A. Nakhaei, Res. Chem. Intermed. 43 (2017) 6367-6378.
[25] A. Allahresani, B. Taheri, M.A. Nasseri, Res. Chem. Intermed. 44 (2018) 1173-1188.
[26] S. Majumdar, A. Chakraborty, S. Bhattacharjee, S. Debnath, D.K. Maiti, Tetrahedron Lett. 57 (2016) 4595-4598.
[27] C. Wu, R. Shen, J. Chen, C. Hu, Bull. Korean Chem. Soc. 34 (2013) 2431-2435.
[28] R.Y. Guo, Z.M. An, L.P. Mo, S.-T. Yang, H.-X. Liu, S.X. Wang, Z.H. Zhang, Tetrahedron 69 (2013) 9931-9938.
[29] Y. Zou, Y. Hu, H. Liu, D. Shi, ACS Comb. Sci. 14 (2012) 38-43.
[30] B. Maheshwar Rao, G. Niranjan Reddy, T. Vijaikumar Reddy, B.L.A. Prabhavathi Devi, R.B.N. Prasad, J.S. Yadav, B.V. Subba Reddy, Tetrahedron Lett. 54 (20) (2013) 2466-2471.
[31] M.A. Nasseri, F. Kamali, B. Zakerinasab, RSC Adv. 5 (2015) 26517-26520.
[32] S. Riyaz, A. Indrasena, A. Naidu, P.K. Dubey, Indian J. Chem. B 53 (2014) 1442-1447.
[33] A. Hasaninejad, N. Golzar, M. Bevrati, A. Zare, M.M.J. Mol. Catal. A: Chem. 372 (2013) 137-150.
[34] L.-M. Wang, N. Jiao, J. Oiu, J.-J. Yu, J.-Q. Liu, F.-L. Guo, Y. Liu. Tetrahedron 66 (2010) 339-343.
[35] M.N. Elinson, R.F. Nasaybullin, F.V. Ryzhkov, T.A. Zaimovskaya, G.I. Nikishi, Monatsh Chem. 146 (2015) 631-635.