An Efficient Solvent Free Microwave Assisted MgFe2O4 Magnetic Nanoparticles Catalyzed Green Protocol Towards Michael Addition

Shobha Bansal, Prabal Pratap Singh
Affiliation: 
1 Department of Chemistry, GLA University, NH-2 Delhi-Mathura Highway Chaumuhan Mathura 281406, India prabal.singh@gla.ac.in
DOI: 
https://doi.org/10.23939/chcht13.01.018
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Abstract: 
MgFe2O4 magnetic nanoparticles were used as an efficient catalyst for the synthesis of Michael products by treating substituted chalcones and β-nitro styrenes with electron donar species like malononitrile and ethyl cyanoacetate in solvent free microwave conditions. In this study, we report that MgFe2O4 magnetic nanoparticles were the best heterogeneous catalyst with 10 mol % loading for synthesis of Michael products as compared to several reported catalysts. The reusability of MgFe2O4 nanoparticles was checked for 5 times without appreciable loss of catalytic activity.
References: 

[1] Gawley R.: Synthesis, 1976, 12, 777. https://doi.org/10.1055/s-1976-24200
[2] Jung M.: Tetrahedron, 1976, 32, 3. https://doi.org/10.1016/0040-4020(76)80016-6
[3] Peters J: Synthesis, 1979, 5, 321 https://doi.org/10.1055/s-1979-28668
[4] Galli C., Marotta E., Right P., Rosini G.: J. Org. Chem., 1995, 60, 6624. https://doi.org/10.1021/jo00125a064
[5] Hanessian S., Pham V.: Org. Lett., 2000, 2, 2975. https://doi.org/10.1021/ol000170g
[6] Sibi M., Manyem S.: Tetrahedron, 2000, 56, 8033. https://doi.org/10.1016/S0040-4020(00)00618-9
[7] Ballini R., Bosica G., Fiorini D., Gil M.: Synthesis, 2004, 4, 605. https://doi.org/10.1055/s-2004-815948
[8] Chandrasekhar S., Rambabu C., Shyamsundar T.: Tetrahedron Lett., 2007, 48, 4683. https://doi.org/10.1016/j.tetlet.2007.05.026
[9] Tomohiro T., Takuya K., Tsutomu I.: Tetrahedron Lett., 2000, 41, 10229. https://doi.org/10.1016/S0040-4039(00)01820-7
[10] Spande T., Garraffo H., Edwards M. et al.: J. Am. Chem. Soc., 1992, 114, 3475. https://doi.org/10.1021/ja00035a048
[11] Taasu K., Mizutani S., Noguchi M. et al.: J. Org. Chem., 2000, 65, 4112. https://doi.org/10.1021/jo000185s
[12] Bergmann E., Ginsburg D., Pappo R.: Org. React. 1959, 10, 179. https://doi.org/10.1002/0471264180.or010.03
[13] Davey W., Gwilt J.: J. Chem. Soc., 1957, 1015. https://doi.org/10.1039/jr9570001015
[14] Garcia-Raso A., Garcia-Raso J., Campaner B. et al.: Synthesis, 1982, 12, 1037. https://doi.org/10.1055/s-1982-30055
[15] Ganesh S., Sarkar A.: Tetrahedron Lett., 1991, 32, 1085. https://doi.org/10.1016/S0040-4039(00)74494-7
[16] Li T-J., Cui Y., Chen G-F. et al.: Synth. Commun., 2003, 33, 353. https://doi.org/10.1081/SCC-120015762
[17] Ye W-P., Xu J-Y., Tan C-T., Tan C-H.: Tetrahedron Lett., 2005, 46, 6875. https://doi.org/10.1016/j.tetlet.2005.08.010
[18] Zahouily M., Bahlaodhuan B., Aadil M. et al.: Org. Pro. Res. Develop., 2004, 8, 275. https://doi.org/10.1021/op034161+
[19] Ma Y-M., Zhang Y-M.: Synth. Commun., 2002, 32, 819. https://doi.org/10.1081/SCC-120002689
[20] Meciarova M., Toma S.: Chem. Eur. J., 2007, 13, 1268. https://doi.org/10.1002/chem.200600870
[21] Gu H., Li J., Qu G. et al.: Chirality, 2011, 23, 514. https://doi.org/10.1002/chir.20956
[22] Rosnati V., Saba A., Salimbeni A.: Tetrahedron Lett., 1981, 22, 167. https://doi.org/10.1016/0040-4039(81)80178-5
[23] Toda F., Takumi H., Nagami M., Tanaka K.: Hetrocycles, 1998, 47, 469. https://doi.org/10.3987/COM-97-S(N)77
[24] Bram G., Sansoulet J., Galons H., Miocque M.: Synth. Commun., 1988, 18, 367. https://doi.org/10.1080/00397918808064000
[25] Kim D., Huh S., Kim S.: Tetrahedron Lett., 2001, 42, 6299. https://doi.org/10.1016/S0040-4039(01)01237-0
[26] Dere R., Pal R., Patil P., Salunkhe M.: Tetrahedron Lett., 2003, 44, 5351. https://doi.org/10.1016/S0040-4039(03)01198-5
[27] Loupy P.: Top. Curr. Chem., 1999, 206, 153. https://doi.org/10.1007/3-540-48664-X_7
[28] Rao H., Jothilingam S.: J. Chem. Sci., 2005, 117, 323. https://doi.org/10.1007/BF02708445
[29] Li J., Cui Y., Chen G. et al.: Synth. Commun., 2003, 33, 353. https://doi.org/10.1081/SCC-120015762
[30] Bansal S., Kumar Y., Pippal P. et al.: New J. Chem., 2017, 41, 2668. https://doi.org/10.1039/C6NJ03701A
[31] Pippal P., Singh P.: Orient. J. Chem., 2017, 33, 1736. https://doi.org/10.13005/ojc/330418
[32] Sharma M., Singh P., Bharadwaj P.: J. Mol. Catal. A: Chem., 2011, 342, 6. https://doi.org/10.1016/j.molcata.2011.04.016
[33] Liang D., Xin X., Gao H. et al.: Chem. Res. Chinese Univ., 2009, 25, 169.
[34] Ying A., Chen X., Wu C. et al.: Synth. Commun., 2012, 42, 3455. https://doi.org/10.1080/00397911.2011.584260
[35] Guo H., Li J., Qu G. et al.: Chirality, 2011, 23, 514. https://doi.org/10.1002/chir.20956
[36] Shen Z., Gu D., Yang J., Ji S.: Synth. Commun., 2011, 41, 851. https://doi.org/10.1080/00397911003707006
[37] Mohammad R., Najmedin A., Elham A., Forogh E.: J. Mol. Catal. A, 2008, 292, 44. https://doi.org/10.1016/j.molcata.2008.06.003
[38] Shi J., Wang M., He L. et al.: Chem. Commun., 2009, 4711. https://doi.org/10.1039/b908632c
[39] Sakthivel V., Kasi P.: Ind. J. Chem. B., 2010, 49, 469.