A simple and green approach for the synthesis of substituted dihydro-2-oxypyrroles catalyzed by nano-Fe3O4@SiO2/SnCl4 superparamagnetic nanoparticles
الموضوعات : Iranian Journal of CatalysisBi Bi Fatemeh Mirjalili 1 , Reza Araqi 2 , Seyed Ahmad Mohajeri 3
1 - Department of Chemistry, College of Science, Yazd University, Yazd, P.O. Box. 89195-741, I. R. Iran.
2 - Department of Chemistry, College of Science, Yazd University, Yazd, P.O. Box. 89195-741, I. R. Iran.
3 - Pharmaceutical Research Center, School of pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran.
الکلمات المفتاحية: Dihydro-2-oxypyrroles, Magnetic catalyst, Fe3O4@SiO2/SnCl4, Heterogeneous acid catalyst, Dialkyl acetylene dicarboxylate,
ملخص المقالة :
In this work, an efficient and green procedure for the synthesis of dihydro-2-oxypyrroles has been developed. One-pot four-component condensation reaction of aniline derivatives (2 mmol), dialkyl acetylene dicarboxylate (1 mmol), and aldehydes ( 1 mmol) was done in ethanol at 65 °C in the presence of nano-Fe3O4@SiO2/SnCl4 as a magnetically reusable heterogeneous acid catalyst. The obtained dihydro-2-oxypyrroles were purified without any chromatography techniques. The structure of obtained pure products was identified by physical properties and spectroscopic data such as FT-IR, 1H NMR, 13C NMR and mass spectroscopy. This protocol consistently has the advantages of excellent yields, short reaction time, simple workup, recyclability of the catalyst up to six runs without appreciable loss of activity.
[1] T. Kawasuji, M. Fuji, T. Yoshinaga, A. Sato, T. Fujiwara, R. Kiyama, Bioorgan. Med. Chem. 15 (2007) 5487-5492.
[2] X. Luo, M. Shu, Y. Wang, J. Liu, W. Yang, Z. Lin, Molecules 17 (2012) 2015-2029.
[3] C. Peifer, R. Selig, K. Kinkel, D. Ott, F. Totzke, C. Schächtele, R. Heidenreich, M. Röcken, D. Schollmeyer, S. Laufer, J. Med. Chem. 51 (2008) 3814-3824.
[4] T.R. Reddy, C. Li, X. Guo, H.K. Myrvang, P.M. Fischer, L.V. Dekker, J. Med. Chem. 54 (2011) 2080-2094.
[5] W. R. Li, S.T. Lin, N.M. Hsu, M.S. Chern, J. Org. Chem. 67 (2002) 4702-4706.
[6] A. Kolocouris, G.B. Foscolos, G. Fytas, J. Neyts, E. Padalko, J. Balzarini, R. Snoeck, G. Andrei, E. De Clercq, J. Med. Chem. 39 (1996) 3307-3318.
[7] A.S. Demir, F. Aydogan, I.M. Akhmedov, Tetrahedron Asym. 13 (2002) 601-605.
[8] Z. Feng, X. Li, G. Zheng, L. Huang, Bioorg. Med. Chem. Lett. 19 (2009) 2112-2115.
[9] L. Zhang, Y. Tan, N.X. Wang, Q.Y. Wu, Z. Xi, G.F. Yang, Bioorg. Med. Chem. 18 (2010) 7948-7956.
[10] S. Tarnavsky, G. Dubinina, S. Golovach, S. Yarmoluk, Biopolym. Cell. 19 (2003) 548-552.
[11] D. Albrecht, B. Basler, T. Bach, J. Org. Chem. 73 (2008) 2345-2356.
[12] A. Dömling, Chem. Rev. 106 (2006) 17-89.
[13] A. Bamoniri, B.F. Mirjlili, R. Tarazian, Monatsh. Chem.146 (2015) 2107-2115.
[14] A.T. Khan, A. Ghosh, M. M. Khan, Tetrahedron Lett. 53 (2012) 2622-2626.
[15] L. Lv, S. Zheng, X. Cai, Z. Chen, Q. Zhu, S. Liu, ACS Comb. Sci. 15 (2013) 183-192.
[16] B.F. Mirjalili, R. Zare Reshquiyea, RSC Adv. 5 (2015)15566-15571.
[17] S. Rana, M. Brown, A. Dutta, A. Bhaumik, C. Mukhopadhyay, Tetrahedron Lett. 54 (2013) 1371-1379.
[18] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, K. Khandan-Barani, J. Chem. Res. 37 (2013) 40-42.
[19] N. Salehi, B.F. Mirjalili, RSC Adv. 7 (2017) 30303-30309.
[20] M. Nickraftar, N. Najafi Hajivar, J. Aboonajmi, E. Fereidooni, Res. Chem. Intermed. 42 (2016) 2899-2908.
[21] S.S. Sajadikhah, M.T. Maghsoodlou, RSC Adv. 4 (2014) 43454-43459.
[22] L. Lv, S. Zheng, X. Cai, Z. Chen, Q. Zhu, S. Liu S, ACS Comb. Sci. 15 (2013) 183-192;
[23] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Chin. Chem. Soc. 60 (2013) 1003-1006.
[24] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, Chin. Chem. Lett. 25 (2014) 58-60.
[25] Q. Zhu, H. Jiang, J. Li, S. Liu, C. Xia, M. Zhang, (2009) J. Comb. Chem. 11 (2009) 685-696.
[26] S.S. Sajadikhah, N. Hazeri, Res. Chem. Intermed. 40 (2014) 737-748.
[27] N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, S. Mohamadian-Souri, M. Norouzia, M. Moein, J. Chin. Chem. Soc. 61 (2014) 217-220.
[28] S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, A.C. Willis, J. Iran. Chem. Soc. 10 (2013) 863-871.
[29] J.N. Zhang, X.H. Yang, W.J. Guo, B. Wang, Z.H. Zhang, Synlett 28 (2017) 734-740.
[30] B.F. Mirjalili, H. Jorsarraie, H. Akrami, Iran. J. Catal. 7 (2017) 201-205.
[31] B.F. Mirjalili, A. Bamoniri, Z. Fazeli, Iran. J. Catal. 6 (2016) 253-259.
[32] B.F. Mirjalili, A. Bamoniri, M.A. Mirhoseini, Iran. J. Catal. 6 (2016) 23-27.
[33] B.F. Mirjalili, A. Bamoniri, S. Fouladgar, Polycycl. Aromat. Compd. 37 (2017) 345-361.
[34] A. Bamoniri, S. Fouladgar, RSC Adv. 5 (2015) 78483-78490.
