Dihydropyrimidinonoes Synthesis via One Pot Solvent-free Cu catalyzed Reaction

Subject Areas :

mohammad kazem mohammadi ¹

1 -

Received: 2024-09-11 Accepted : 2024-09-29 Published : 2024-07-18

Keywords: Biginelli, Dihydropyrimidinones, One-pot, Solvent-free, CuCl2 ,

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. we now wish to report a facile and rapid one-pot solvent free three component procedure preparation of DHPMs derivatives with CuCl2 as a non-toxic, reusable, inexpensive and easily available reagent, under solvent-free conditions at the range of temperatures.

we now wish to report a facile and rapid one-pot solvent free three component procedure preparation of DHPMs derivatives with CuCl₂ as a non-toxic, reusable, inexpensive and easily available reagent, under solvent-free conditions at the range of temperatures.

 

References:

[1] Biginelli, P. Gazz. Chim. Ital. 1893 , 360 , 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) Matsuda,T.; Hirao, I.; Kagalku Zasshi, N. 1965 ,1195 , 86; (b) B.B. Snider,J. Chen,A.D. Patil,A. Freyer, Tetrahedron Lett. 6977–6980 (1996) 37.
[7]. Maiti,G.; Kundu,P.; Guin, C. Tetrahedron Lett. 2003 , 44 , 2757.
[8]. Shaabani, A .; Bazgir,A.; Teimouri, F. Tetrahedron Lett. 2003 , 44 , 857.
[9]. Salehi,H.; Guo,Q.-X. Synth. Commun. 2004 , 34 , 171.
[10]. Lu,J.; Bai,Y. Synthesis. 2002 , 466.
[11]. Kumar,K.A. ; Kasthuraiah, M.; Reddy,C.S.; Reddy, C.D. Tetrahedron
Lett. 2001, 42 , 7873.
[12].Fu,N.-Y.; Yuan,Y.F.; Cao,Z.; Wang,S.-W. ; Wang,J.-T.; Peppe,C.
Tetrahedron. 2002, 58 ,4801.
[13]. Jenner,G. Tetrahedron Lett. 2004, 45, 6195.
[14]. Narsaiah,A.V.; Basak,A.K.; Nagaiah,K. Synthesis , 2004 , 1253.
[15]. Kalita,H.R.; Phukan,P. Catal. Commun. 2007, 8, 179.
[16]. Yadav,J.S.; Reddy,B.V.S.; Srinivas,R.; Venugopal, C. ; Ramalingam,T.
Synthesis ,2001, 1341.
[17]. Gohain, M.; Prajapati,D.; Sandhu, J.S.; Synlett , 2004, 235.
[18]. Paraskar, A.S. ; DewKar,G.K.; Sudalai,A. Tetrahedron Lett. 2003 ,44
, 3305.
[19]. Khodaei,M.M.; Salehi,P.; Zolfigol,M.A.; Sirouszadeh, S.; Pol. J. Chem. 2004 , 78 , 385.
[20]. Bose,D.S.; Kumar,R.K.; Fatima,L. Synlett ,2004, 279.
[21]. Azizian,J.; Mohammadi, M. K.; Firuzi, O.R.; Mirza, B.; Miri , R. Chem Biol Drug Des . 2010,75, 375–380
[22]. Azizian, J.; Miri, R.; Mohammadi, M. K.; Sheikholeslami Farahani, F.; Hosseini, J.; Nikpour, M . Phosphorus, Sulfur, and Silicon, 2010, 185,1782–1787,