Green procedure for synthesis of 3, 4 dihydropyrimidinones using 12-molybdophosphoric acid, as a catalyst and solvent free condition under microwave irradiation
محورهای موضوعی : شیمی تجزیه
Hojjatollah Salehi
1
(Nuclear Fuel Cycle Research School, Nuclear Science and Technology Research Institute,
AEOI,P.O.Box 11365-8466, Tehran, Iran)
کلید واژه: Solvent-free, Biginelli reaction, Microwave-irradiation, One-pot synthesis, Dihydropyrimidinones, 12-molybdophosphoric acid,
چکیده مقاله :
Simple and improved conditions have been found to carry out the Biginelli reaction for the synthesis of 3, 4-dihydropyrimidin-2(1H) - one derivatives. This synthesis was performed in the presence of 12-molybdophosphoric acid (H3PMo12O40) as catalyst. These reactions were performed under solvent free conditions with microwave irradiation as the energy source. Compared with the classical Biginelli reaction conditions, this new method has the advantage of excellent yields (76–96%). The advantages of this novel protocol include the excellent yield, operational simplicity, short time, and the avoidance of the use of organic solvents and friendly preparation. Products were identified using physical and spectroscopic data.
[1] Kochi, M.; Green Reaction Media for Organic
Synthesis, Blackwell; 2005.
[2] Seddon, K.R.; Nature; 2 , 363; 2003.
[3] Sheldon, R.A.; Bekkum, H.; Van. Fine Chemicals through Heterogeneous Catalysis, Wiely-VCH, 2002.
[4] Kappe, C.O.; Tetrahedron; 43, 6937;1993.
[5] Kappe, C.O.; Acc. Chem. Res.; 33, 879; 2000.
[6] Kappe, C.O.; Eur. J. Med. Chem.; 35, 1043; 2000.
[7] Pourjavadi, A. ; Salimi, H.; Barzegar, Sh.; Eftekhari, B.; Acta Chim. Slov.; 54, 140-143; 2007.
[8] Biginelli, P.; Gazz. Chim. Ital.; 23, 360 ;1893.
[9] Zumpe, F.L.; Fluss, M.; Schmitz, K.; Lender, A. ;
Tetrahedron Lett.; 48, 1421-1423; 2007.
[10] Zhang, M. ; Li, Y.-Q.; Zhou, M.-Y. ; Chin. J. Chem.; 24, 282-284; 2006.
[11] Zhidovinova, M.S.; Fedorova, O.V.; Rusinov, G.L.; Ovchinnikova, I.G.; Russian Chem. Bull.; 52, 2527-2528; 2003.
[12] Alessandro, D.; Alessandro, M. ;Tetrahedron Lett.; 42, 7975-7978; 2001.
[13] Han, X.; Xu, F. ; Luo, Y.; Shen, Q. ; J. Org. Chem.; 28, 1500-1503; 2005.
[14] Reddy, C.V.; Mahesh, M.; Raju, P.V.K.; Babu, T.R.; Reddy, V.V.N.; Tetrahedron Lett.; 43, 2657-2659; 2002.
[15] Narsaiah, A.V. ; Basak, A.K.; Synthesis; 35, 1253–1256; 2004,.
[16] Shao, G.; Hecheng Huaxue,; 12, 325 -328; 2004.
[17] Salehi, H.H.; Guo, Q.-X.; Synth Commun.; 34,
171–179; 2004.
[18] Rafiee, E.; Shahbazi, F.; J. Mol. Catal. A: Chem.; 250, 57; 2006.
[19] Choudhary, VR.; Tillu, VH.; Narkhede, VS.; Borate, HB.; Warkharkar, RD.; Catal.commun.; 4, 499-453; 2009
[20] Meradur, S.P.; Gokavi, G.S.; Catal. Commun.; 8 , 279; 2007.
[21] (a) Fazaeli, R.; Tangestaninejad, S.; Aliyan, H.; Moghadam, M.; Appl. Catal. A: Gen.; 4, 309; 2006. (b) Heravi, M.M.; Sadjadi, S.; J. Iran. Chem. Soc.; 6, 1-54, 2009.
[22] Zumpe, F.L.; Flub, M.; Schmitz, K.; Lender, A.;
Tetrahedron Lett. ; 48, 1421; 2007.
[23] Gupta, R.; Paul, S. ; Gupta, R. ;J. Mol. Catal. A: Chem.; 266, 50; 2007.
[24] Desai, B. ; Dallinger, D. ; Kappe, C.O. ; Tetrahedron; 62, 4651-4664; 2006.
[25] Katritzky, A.R.; Singh, S.K.; Arkivoc.; xiii, 68-76; 2003.
[26] Zhu, Y.; Pan, Y.; Huang, S.; Synth. Commun.; 34, 3167-3174; 2004.
[27] Wang, Z.; Xu, L.; Xia, C.; Wang, H. Tetrahedron Lett.; 45,7951–7953;2004.
[28] Salehi, H.; Guo, Q.-X. ; Synth. Commun.; 34,
4349-4356; 2004.
[29] Kappe, C.O.; J. Org. Chem.; 62, 7201-7208; 1997.
[30] Folkers, K.; Johnson, T.B.; J. Am. Chem. Soc.; 55, 3784 -3791; 1933.
[31] Reddy, Y.T.; Rajitha, B.; Reddy, P.N.; Kumar, B.S.; Rao, V.P.; Synth. Commun.; 34, 3821-3825.; 2004.
[32] Salehi, H.; Guo, Q.-X. ; Chin. J. Chem.; 23, 1, 91-97; 2005.
[33] Lu, J.; Bai, Y. Synthesis; 466-470, 2002.
