Abstract
Dodecylphosphonic acid is a solid Bronsted acid that catalyzes efficiently the preparation of dihydropyrimidinones by Biginelli condensation under solvent-free conditions. This protocol offers several advantages including high yields, short reaction times, easy work-up, and use of cheap, relatively moderate acidic and safe catalyst.
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References
C.O. Kappe, Acc. Chem. Res. 33 (2000) 879.
C.O. Kappe, Tetrahedron 49 (1993) 6937.
C.O. Kappe, Eur. J. Med. Chem. 35 (2000) 1043.
P. Biginelli, Gazz. Chim. Ital. 23 (1893) 360.
H. Khabazzadeh, K. Saidi, H. Sheibani, Bioorg. Med. Chem. Lett. 18 (2008) 278.
S.L. Jain, V.V.D.N. Prasad, B. Sain, Catal. Commun. 9 (2008) 499.
I. Cepanec, M. Litvić, M. Filipan- Litvić, I. Grüngold, Tetrahedron 63 (2007) 11822.
A. Kamal, T. Krishnaji, M.A. Azhar, Catal. Commun. 8 (2007) 1929.
B.K. Banik, A.T. Reddy, A. Datta, C. Mukhopadhyay, Tetrahedron Lett. 48 (2007) 7392.
H. Adibi, H.A. Samimi, M. Beygzadeh, Catal. Commun. 8 (2007) 2119.
N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor, B.M. Bhanage, J. Mol. Catal. A: Chem. 14 (2007) 271.
N. Ahmed, J.E. Lier, Tetrahedron Lett. 48 (2007) 5407.
M.A. Bigdeli, S. Jafari, G.H. Mahdavinia, H. Hazarkhani, Catal. Commun. 8 (2007) 1641.
V. Polshettiwar, R.S. Varma, Tetrahedron Lett. 48 (2007) 7343.
Y. Yu, D. Liu, C. Liu, G. Luo, Bioorg. Med. Chem. Lett. 17 (2007) 3508.
T. Jin, S. Zhang, T. Li, Synth. Commun. 32 (2002) 1847.
F. Bigi, S. Carloni, B. Frullanti, R. Maggi, G. Sartori, Tetrahedron Lett. 40 (1999) 3465.
E.H. Hu, D.R. Sidler, U.-H. Dolling, J. Org. Chem. 63 (1998) 3453.
P. Salehi, M. Dabiri, M.A. Zolfigol, M.A. Bodaghi Fard, Tetrahedron Lett. 44 (2003) 2889.
Z. Hassani, M.R. Islami, M. Kalantari, Bioorg. Med. Chem. Lett. 16 (2006) 4479.
L. Ismaili, A. Nadaradjane, L. Nicod, C. Guyon, A. Xicluna, J.F. Robert, B. Refouvelet, Eur. J. Med. Chem. (2007) 1.
W.-Y. Chen, S. Qin, J.R. Jin, Catal. Commun. 8 (2007) 123.
X.-H. Chen, X.-Y. Xu, H. Liu, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 128 (2006) 14802.
M.M. Heravi, F. Derikvand, F.F. Bamoharram, J. Mol. Cata. A: Chem. 242 (2005) 173.
M.M. Heravi, K. Bakhtiari, F.F. Bamoharram, Catal. Commun. 7 (2006) 373.
H. Sharghi, M. Jokar, Synth. Commun. 50 (2009) 958.
S. Ghassamipour, A.R. Sardarian, Tetrahedron Lett. 50 (2009) 514.
A. Shaabani, A. Bazgir, F. Teimuri, Tetrahedron Lett. 44 (2003) 857.
F. Shirini, K. Marjani, H. Taherpour Nahzomi, ARKIVOC i (2007) 51.
F. Bigi, S. Carloni, B. Frullanti, R. Maggi, G. Sartori, Tetrahedron Lett. 40 (1999) 3465.
J.S. Yadav, B.V.S. Reddy, R. Srinivas, C. Venogopal, T. Ramalingam, Synthesis (2001) 1341.
K.Y. Lee, L.Y. Ko, Bull. Korean Chem. Soc. 25 (2004) 1929.
N.F. Fu, Y.F. Yuan, Z. Cao, Z.W. Wang, J.T. Wang, C. Peppe, Tetrahedron 58 (2002) 4801.
S. Xue, Y.C. Shen, Y.L. Li, X.M. Shen, Q.X. Guo, Chin. J. Chem. 20 (2002) 385.
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Ghassamipour, S., Sardarian, A.R. One-Pot synthesis of dihydropyrimidinones by dodecylphosphonic acid as solid Bronsted Acid Catalyst under Solvent-Free Conditions via Biginelli condensation. JICS 7, 237–242 (2010). https://doi.org/10.1007/BF03245884
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DOI: https://doi.org/10.1007/BF03245884