1
774
L. Wang and C. Cai
Vol 45
under vacuum overnight. Complex formation was demonstrated
by a new bond at 1629 cm in the IR spectrum. The aluminium
[11] Zhu, Y.-L.; Huang, S.-L.; Pan, Y.-J. Eur. J. Org. Chem.
-1
2
005, 2354.
12] Yadav, J. S.; Reddy, B.V. S.; Srinivas, R.; Venugopal, C.;
Ramalingam, T. Synthesis 2001, 9, 1341.
13] Maiti, G.; Kundua, P.; Guin, C. Tetrahedron Lett. 2003, 44,
757.
14] Yadav, J. S.; Reddy, B. V. S.; Sridhar, P.; Reddy, J. S. S.;
[
content of Ps–AlCl was 2.11% analyzed by ICP analysis and
3
the loading capacity of aluminium chloride was calculated to be
[
0
.78 mmol/g.
2
Typical procedure for the synthesis of 3,4-dihydro-
[
pyrimidin-2(1H)-ones. A mixture of benzaldehyde (1.06 g, 10
mmol), ethyl acetoacetate (1.30 g, 10 mmol), urea (0.9 g, 15
mmol) and Ps–AlCl (1.28 g, 1 mmol of AlCl ) in ethanol (10
mL) was refluxed for 3 h. After completion of reaction, hot
ethanol was added to the mixture; the catalyst was filtrated off
and washed with ether (15 mLꢀ2). The filtrate was concentrated
on a rotary evaporator under reduced pressure and the solid
product obtained was washed with water (20 mLꢀ2), and
recrystallized from ethanol or ethyl acetate/n-hexane to give
Nagaiah, K.; Lingaiah, N.; Saiprasad, P. S. Eur. J. Org. Chem. 2004,
552.
[15] Abelman, M. M.; Smith, S. C.; James, D. R. Tetrahedron
Lett. 2003, 44, 4559.
3
3
[16] Lu, J; Ma, H. Synlett 2000, 63.
[17] Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Fard, M. A. B.
Tetrahedron Lett. 2003, 44, 2889.
18a] Arfan, A.; Paquin, L.; Bazureau, J. P. Russian J. Org. Chem.
007, 43, 1058; [b] Legeay, J. C.; Eynde, J. J. V.; Bazureau, J. P.
[
2
Tetrahedron 2005, 61, 12386.
5
2
-ethoxy-carbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-
(1H)-one in 89% yield, mp 203-204 ꢁ (202-204 ꢁ) [4]. Other
[19] Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.;
Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.;
Taylor, S. J. J. Chem. Soc. Perkin Trans. 1 2000, 3815 and references
cited therein.
aldehydes were reacted with urea and ꢂ-dicarbonyl compound
similarly. The products were characterized by mp, IR, and H
NMR and they are also compared with respect to authentic
compounds available in literature.
1
[
20] Leadbeater, N. E.; Macro, M. Chem. Rev. 2002, 102, 3217.
[
21a] Neckers, D. C.; Kooistra, D. A.; Green, G. W. J. Am. Chem.
Soc. 1972, 9284; [b] Blossey, E. C.; Turner, L. M.; Neckers, D. C.
Tetrahedron Lett. 1973, 26, 1823; [c] Blossey, E. C.; Turner, L. M.;
Neckers, D. C. J. Org. Chem. 1975, 40, 959.
Acknowledgement. We thank Nanjing Microspheres Hi-
Efficiency Isolation Carrier Co., Ltd for providing polystyrene
and the National Defense Committee of Science and Technology
of China (40406020301) for financial support.
[
22] Deshmukh, A. P.; Padiya, K. J.; Salunkhe, M. M. J. Chem.
Research(S) 1999, 568.
[23] Borujeni, K. P.; Tamami, B. Catal. Commun. 2007, 8, 1191.
[24] Borujeni, K. P.; Tamami, B. Tetrahedron Lett. 2004, 45, 715.
[25] Tamami, B.; Borujeni, K. P. Iran. Polym. J. 2003, 12, 507.
[26] Wang, L.; Cai, C. Chin. J. Appl. Chem. 2008, 25, inpress.
[27] Shi, L.; Zhu, G.-H.; Ding, X.-Y.; Li, J.-H.; Jing, X.-H.; Hua,
REFERENCES
[
1] Kappe, C. O.; Shishkin, O. V.; Uray, G.; Verdino, P.
P. Chin. Chem. Reagent 2007, 29, 255.
Tetrahedron 2000, 56, 1859.
[28] Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G.
[
[
[
2] Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
3] Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
4] Hu, E. H.; Sidler, D. R.; Dolling, U. H. J. Org. Chem. 1998,
Tetrahedron Lett. 1999, 40, 3465.
[29] Kumar, A.; Maurya, R. A. Tetrahedron Lett. 2007, 48, 4569.
[30] Fu, N.-Y.; Yuan, Y.-F.; Cao, Z.; Wang, S.-W.; Wang, J.;
Peppe, T. C. Tetrahedron 2002, 58, 4801.
6
2
6
6
2
2
2
3, 3454.
[
5] Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett.
[31] Niknam, K.; Zolfigol, M. A.; Hossieninejad, Z.; Daneshvar,
N. Chin. J. Catal. 2007, 28, 591.
[32] Zumpe, F. L.; Schmitz, K.; Lender, A. Tetrahedron Lett.
2007, 48, 1421.
[33] Wang, M.; Jiang, H.; Wang, Z.-C. J. Chem. Research(s).
2005, 691.
[34] Eynde, J. J. V.; Audicart, N.; Canonne, V.; Michel, S.;
Haverbeke, Y. V.; Kappe, C. O. Heterocycles 1997, 45, 1967.
[35] Su, W.-K.; Li, J.-J.; Zheng, Z.-G.; Shen, Y.-C. Tetrahedron
Lett. 2005, 46, 6037.
[36] Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem., 2000,
65, 3864.
000, 41, 9075.
[6] Bose, D. S.; Fatima, L.; Mereyala, H. B. J. Org. Chem. 2003,
8, 587.
[
7] Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65,
270.
[8] Rafiee, E.; Jafari, H. Bioorg. Med. Chem. Lett. 2006, 16,
463.
[9] Ramalinga, K.; Vijayalakshmi, P.; Kaimala, T. N. B. Synlett
001, 863.
[
10] Paraskar, A. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett.
003, 44, 3305.