Biginelli Synthesis and Theoritical Study of Dihydropyrimidinones
Subject Areas :Mohammad Hosein Farjam 1 , Ramin Rezaei 2
1 - Department of Chemistry , Firoozabad Branch, Islamic Azad University,Firoozabad, Iran.
2 - Department of Chemistry , Firoozabad Branch, Islamic Azad University,Firoozabad, Iran.
Keywords: Solvent-free, One-pot, Biginelli reaction, Dihydropyrimidinones,
Abstract :
An effective one-pot synthesis of dihydropyrimidinonoes in solvent free conditions using CuCl2 as an inexpensive and readily available reagent through Biginelli condensation reaction of aldehyde derivatives, 1,3-dicarbonyl compounds and urea is described. Excellent yields, short reaction times for formation of the products and simple work-up are attractive features of this green protocol.
[1] P. Biginelli, Gazz. Chim. Ital. 360 (1893) 23;
[2] Kappe, C.O. Tetrahedron.1993, 49, 6937.
[3] Rovnyak, G.C.; Kimball, S. D.; Beyer, B.;Cucinotta, G.;DiMarco, J. D.;Gougoutas, J. Z.;Hedberg, A.;Malley, M. F.; McCarthy, J. P.; Zhang R.; Moreland,S.J. Med. Chem. 1995,38,119 .
[4] Overman, L.E.;RabinowitzM. H.;Renhowe,P.A.J. Am. Chem. Soc.1995, 117, 2657.
[5] Mayer, T.U.;Kapoor,T.M.;Haggarty, S.J.; King,R.W.; Schreiber,S.L.;Mitchison,T.J. Science. 1999,286, 971.
[6] (a) T. Matsuda,I. Hirao, Nippon Kagalku Zasshi 1195 (1965) 86; (b) B.B. Snider,J. Chen,A.D. Patil,A. Freyer, Tetrahedron Lett. 6977– 6980 (1996) 37.
[7] G. Maiti, P. Kundu, C. Guin, Tetrahedron Lett. 44 (2003) 2757.
[8] A. Shaabani, A. Bazgir, F. Teimouri, Tetrahedron Lett. 44 (2003) 857.
[9] H. Salehi, Q.-X. Guo, Synth. Commun. 34 (2004) 171.
[10] J. Lu, Y. Bai, Synthesis (2002) 466.
[11] K.A. Kumar, M. Kasthuraiah, C.S. Reddy, C.D. Reddy, Tetrahedron
Lett. 42 (2001) 7873.
[12] N.-Y. Fu, Y.F. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang, C. Peppe,
Tetrahedron 58 (2002) 4801.
[13] G. Jenner, Tetrahedron Lett. 45 (2004) 6195.
[14] A.V. Narsaiah, A.K. Basak, K. Nagaiah, Synthesis (2004) 1253.
[15] H.R. Kalita, P. Phukan, Catal. Commun. 8 (2007) 179.
[16] J.S. Yadav, B.V.S. Reddy, R. Srinivas, C. Venugopal, T. Ramalingam,
Synthesis (2001) 1341.
[17] M. Gohain, D. Prajapati, J.S. Sandhu, Synlett (2004) 235.
[18] A.S. Paraskar, G.K. DewKar, A. Sudalai, Tetrahedron Lett. 44
(2003) 3305.
[119] M.M. Khodaei, P. Salehi, M.A. Zolfigol, S. Sirouszadeh, Pol. J.
Chem. 78 (2004) 385.
[20] D.S. Bose, R.K. Kumar, L. Fatima, Synlett (2004) 279.
[21]Javad Azizian, Mohammad K. Mohammadi, Omidreza Firuzi, Behrooz Mirza and Ramin Miri Chem Biol Drug Des 2010; 75: 375–380
[22]Javad Azizian, Ramin Miri, Mohammad Kazem Mohammadi, Fatemeh Sheikholeslami Farahani, Javad Hosseini, and Mohsen Nikpour . Phosphorus, Sulfur, and Silicon, 185:1782–1787, 2010