3510
Y. Yu et al. / Bioorg. Med. Chem. Lett. 17 (2007) 3508–3510
Chem. 1991, 34, 806; (b) Grover, G. J.; Dzwonczyk, S.;
McMullen, D. M.; Normadinam, C. S.; Sleph, P. G.;
Moreland, S. J. J. Cardiovasc. Pharmacol. 1995, 26, 289.
7.76 (s, 1H, NH), 7.39-7.25 (m, 4H, C
CH), 3.96 (q, J = 7.0 Hz, 2H, OCH CH
CH ), 1.09 (t, J = 7.0 Hz, 3H, OCH CH ).
6
H
4
), 5.14 (s, 1H,
), 2.24 (s, 3H,
2
3
3
2
3
3
4
. Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
. Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A.
J. Am. Chem. Soc. 1995, 117, 2657.
5-Ethoxycarbonyl-6-methyl-4-(2,4-dichlorophenyl)-3,4-dihy-
dropyrimidin-2(1H)-one (4e). IR (KBr): 3360, 1698, 1645,
À1
1
875, 816 cm
,
6
H NMR (DMSO-d ): d = 9.35(s, 1H,
5
6
. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
NH), 7.79(s, 1H, NH), 7.52(s, 1H, arom CH), 7.42 (d,
J = 8.4 Hz, 1H, arom CH), 7.36(d, J = 8.4 Hz, 1H, arom
CH), 5.63 (s, 1H, CH), 3.90 (q, J = 7.1 Hz, 2H,
OCH CH ), 2.28 (s, 3H, CH ), 1.02 (t, J = 7.1 Hz, 3H,
. Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Babu, T. R.;
Reddy, V. V. N. Tetrahedron Lett. 2002, 43, 2657.
. Fu, N. Y.; Yuan, Y. F.; Cao, Z.; Wang, S. W.; Wang, J.
T.; Peppe, C. Tetrahedron Lett. 2002, 58, 4801.
7
2
2
3
3
3
OCH
CH
).
8
9
. Dondoni, A.; Massi, A. Tetrahedron Lett. 2001, 42, 7975.
. Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 5917.
5-Ethoxycarbonyl-6-methyl-4-propyl-3,4-dihydropyrimidin-
2(1H)-one (4f). IR (KBr): 3251, 3120, 2958, 2935, 2874,
À1
1
1
1
1
1
1
1
0. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Raj, K. S.;
Prasad, A. R. J. Chem. Soc., Perkin Trans. 1 2001, 1939.
1. Kumar, K. A.; Kasthuraiah, M.; Reddy, C. S.; Reddy, C.
D. Tetrahedron Lett. 2001, 42, 7873.
1720, 1647 cm , H NMR (DMSO-d ): d = 8.93 (s, 1H,
6
NH), 7.32 (s, 1H, NH), 4.10–4.04 (q, J = 4.7 Hz, 3H, H-4
and OCH
CH CH CH
0.87-0.83 (t, J = 6.9 Hz, 3H, CH CH CH ).
2
CH
3
), 2.15 (s, 3H, CH
3
), 1.26–1.40 (m, 4H,
2
2
3
), 1.21–1.16 (t, J = 4.7 Hz 3 H, OCH
CH ),
2 3
2. Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem. 2000,
2
2
3
6
5, 3864.
3. Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65,
270.
5-Methoxycarbonyl-6-methyl-4-(4-chlorophenyl)-3,4-dihy-
dropyrimidin-2(1H)-one (4i). IR (KBr): 3366, 1716,
À1
1
6
1636 cm , H NMR (DMSO-d ): d = 9.27 (s, 1H, NH),
6
4. Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron
Lett. 2000, 41, 9075.
5. Paraskar, A. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron
Lett. 2003, 44, 3305.
7.74 (s, 1H, NH), 7.41–7.22 (m, 4H, C H ), 5.14 (s, 1H,
6
4
3 3
CH), 3.53 (s, 3H, CH OCO), 2.24 (s, 3H, CH ).
5-Methoxycarbonyl-6-methyl-4-(2,4-dichlorophenyl)-3,4-
dihydropyrimidin-2(1H)-one (4l). IR (KBr): 3362, 1697,
À1
1
1
6. Jin, T.; Zhang, S.; Li, T. Synth. Commun. 2002, 32, 1847.
7. Tu, S.; e Fang, F.; Zhu, S.; Li, T.; Zhang, X.; Zhuang, Q.
Synlett 2004, 537.
1647, 845, 820 cm , H NMR (DMSO-d ): d = 9.33 (s,
6
1
1 H, NH), 7.78 ( s, 1H, NH), 7.57 (s, 1H, arom CH), 7.38
(d, J = 8.4 Hz, 1H, arom CH), 7.30 (d, J = 8.4 Hz, 1H,
1
1
2
2
2
8. Salehi, P.; Dabiri, M.; Zolfigolc, M. A.; Fard, M. A. B.
Tetrahedron Lett. 2003, 44, 2889.
9. Heravi, M. M.; Derikvand, F.; Bamoharram, F. F. J. Mol.
Catal. A: Chem. 2005, 242, 173.
0. Heravi, M. M.; Bakhtiari, K.; Bamoharram, F. F. Catal.
Commun. 2006, 7, 373.
1. Zhou, H.; He, M.; Liu, C.; Luo, G. Lett. Org. Chem. 2006,
arom CH), 5.60 (s, 1H, CH), 3.48 (s, 3H, CH OCO), 2.57
3
(s, 3H, CH ).
3
24. Li, J. T.; Han, J. F.; Yang, J. H.; Li, T. S. Ultrason.
Sonochem. 2003, 10, 119.
25. Yarapathi, R. V.; Kurva, S.; Tammishetti, S. Catal.
Commun. 2004, 5, 511.
26. Gohain, M.; Prajapati, D.; Sandhub, S. J. Synlett 2004,
235.
27. Salehi, H.; Guo, Q. X. Synth. Commun. 2004, 34, 171.
28. Wang, M.; Jiang, H.; Wang, Z. J. Chem. Res., Synop.
2005, 691.
29. Sun, Q.; Wang, Y. Q.; Ge, Z. M.; Cheng, T. M.; Li, R. T.
Synthesis 2004, 1047.
30. Ahmad, S.; Ayoob, B.; Fatemeh, T. Tetrahedron Lett.
2003, 44, 857.
3, 225.
2. A mixture of aldehyde (25 mmol), 1,3-dicarbonyl com-
pounds (27.5 mmol), urea or thiourea (37.5 mmol) and
chloroacetic acid (2.5 mmol) under solvent-free conditions
was heated to 90 °C for the required time in a 100 mL
conical flask in water bath. After cooling, the reaction
mixture was poured into crushed ice and stirred for 5–
10 min. The solid was filtered under suction, washed with
ice-cold water and then recrystallized from ethanol to
afford pure product.
3. Some selected data are as follows:
31. Xue, S.; Shen, Y. C.; Li, Y. L.; Shen, X. M.; Guo, Q. X.
Chin. J. Chem. 2002, 20, 385.
32. Gangadasu, B.; Palaniappan, S.; Rao, V. J. Synlett 2004,
1285.
33. Anup, K. M.; Geetanjali, A.; Soni, K. M. Indian J. Chem.,
Sect. B 2004, 43, 2018.
2
5
dropyrimidin-2(1H)-one (4b). IR (KBr): 3243, 1724, 1647,
-Ethoxycarbonyl-6-methyl-4-(4-chlorophenyl)-3,4-dihy-
À1
1
8
40 cm , H NMR (DMSO-d ): d = 9.26 (s, 1H, NH),
6