BF3/nano-γ-Al2O3 Promoted Knoevenagel Condensation at Room Temperature

Document Type : Research Paper

Authors

1 Department of Chemistry, College of Science, Yazd University, Yazd, P.O. Box 8915813149,I.R.Iran.

2 Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, I.R.Iran.

10.7508/jns.2015.04.007

Abstract

The Knoevenagel condensation of aromatic aldehydes with barbituric acid, dimedone and malononitrile occurred in the presence of BF3/nano-γ-Al2O3 at room temperature in ethanol. This catalyst is characterized by powder X-ray diffraction (XRD), fourier transform infrared spectroscopy (FT-IR), thermal gravimetric analysis (TGA), field emission scanning electron microscopy (FESEM) and energy-dispersive X-ray spectroscopy (EDS).

Keywords


[1] G. Jones, Org. Reac. 15 (1967) 204-273.
[2] F. Texier-Boullet, A. Foucaud, Tetrahedron Lett. 23 (1982) 4927-4928.
[3] S. Chalais, P. Laszlo, A. Mathy, Tetrahedron Lett. 26 (1985) 4453-4454.
[4] F. Freeman, Chem. Rev. 80 (1980) 329-350.
[5] G. Marciniak, A. Delgado, G. Leclerc, J. Velly, N. Decker, J. Schwartz, J. Med. Chem. 32 (1982) 1402-1407.
[6] L.F. Tietze, Chem. Rev. 96 (1996) 115-136.
[7] D. Enders, E. Muller, A.S. Demir, Tetrahedron Lett. 29 (1988) 6437-6440.
[8] S. Liu, Y. Ni, Chinese J. Chem. 32 (2014) 343-348.
[9] J. Xu, K. Shen, B. Xue, Y.X. Li, Y. Cao, Catal. Lett. 143 (2013) 600-609.
[10] K. Mangala, K. Sreekumar, Appl. Org. Chem. 27 (2013) 73-78.
[11] B. Xue, J. Zhu, N. Liu, Y. Li,Catal.Commun. 64 (2015) 105-109.
[12] Y. Ogiwar, K. Takahashi, T. Kitazawa, N. Sakai, J. Org. Chem. 80 (2015) 3101-3110.
[13] A. Alizadeh, M.M. Khodaei, D. Kordestani, A.H. Fallah, M. Beygzadeh, Micropor. Mesopor. Mat. 159 (2012) 9-16.
[14] M. Opanasenko, A. Dhakshinamoorthy, M. Shamzhy, P. Nachtigall, M. Horacek, H. Garcia, J. Cejka, Catal. Sci. Technol. 3 (2013) 500-507.
[15] A. Zhu, R. Liu, L. Li, L. Wang, J. Wang, Catal. Today 200 (2013) 17-23.
[16] G.W. Li, J. Xiao, W.Q. Zhang, Chinese. Chem. Lett. 24 (2013) 52-54.
[17] J. Yang, A. Zheng, M. Zhang, Q. Luo, Y. Yue, C. Ye, X. Lu, F. Deng, J. Phys. Chem. B, 109 (2005) 13124-13131.
[18] M. Sarvari, H. Sharghi, S. Etemad, Chinese J. Chem. 25 (2007) 1563-1567.
[19] D.C. Forbes, A. M. Law, D.W. Morrison, Tetrahedron Lett. 47 (2006) 1699-1703.
[20] F. Dong, Y.Q. Li, R.F. Dai, Chinese Chem. Lett. 18 (2007) 266-268.
[21] R.J. Kalbasi, N. Mosaddegh, Catal.Commun, 12 (2011) 1231-1237.
[22] J-J. Yu, L.M. Wang, J-Q.Liu, F-L.Guo, Y. Liu, N. Jiao, Green Chem. 12 (2010) 216-219.
[23] N. Nagaraijan, S.J. Shenoy, Indian J. Chem, 31 (1992) 73-87.
[24] G. Kaupp, M.R. Naimi-Jamal, J. Schmeyers, Tetrahedron 59 (2003) 3753-3760.
[25] A. Khalafi-Nezhad, A. Hashemi, Iran. J. Chem. Chem. Eng, 20 (2001) 9-11.
[26] S. Kamble, G. Rashinkar, A. Kumbhar, K. Mote, R. Salunkhe, Arch. Apll. Sci. Res. 2 (2010) 217-222.