Biginelli Synthesis and Theoritical Study of Dihydropyrimidinones

Journal of Chemical Reactivity and Synthesis

مقاله 6، دوره 6، شماره 1، شهریور 2016، صفحه 50-55   

نوع مقاله: Research Article

نویسندگان

Mohammad Hosein Farjam^* ؛ Ramin Rezaei

Department of Chemistry , Firoozabad Branch, Islamic Azad University,Firoozabad, Iran.

چکیده

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.

کلیدواژه‌ها

Biginelli reaction؛ Dihydropyrimidinones؛ One-pot؛ Solvent-free

مراجع

[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