6040
W. Su et al. / Tetrahedron Letters 46 (2005) 6037–6040
1
3
1
1
1
1
1
2. Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron
Lett. 2000, 41, 9075–9078.
3. Ranu, B. C.; Hazra, A.; Jana, U. J. Org. Chem. 2000, 65,
3 6
3H, CH ). C NMR (100 MHz, DMSO-d ): d 165.9,
152.2, 148.2, 147.3, 145.8, 135.6, 118.1, 115.2, 110.8, 99.2,
55.5, 53.4, 50.7, 17.7. IR (KBr): 3396, 3116, 3260, 2955,
À1
+
6270–6276.
1679, 1649, 1519 cm . MS (ESI): m/z 291.1 (MÀH ).
4. Paraskar, A. S.; Dewker, G. K.; Sudalai, A. Tetrahedron
Lett. 2003, 44, 3305–3308.
5. Ghosh, R.; Maiti, S.; Chakraborty, A. J. Mol. Catal. A:
Chem. 2004, 217, 47–50.
Anal. Calcd for C14 : C, 57.53; H, 5.52; N; 9.58.
16 2 5
H N O
Found: C, 57.60; H, 5.54; N; 9.50.
Methyl 4-(4-hydroxy-3-methoxy-5-nitrophenyl)-6-methyl-
1
2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (4p):
NMR (400 MHz, DMSO-d
1H, NH), 7.81 (s, 1H, NH), 7.23(s, 1H, ArH), 7.17 (s, 1H,
ArH), 5.17 (s, 1H, CH), 3.86 (s, 3H, OCH ), 3.06 (s, 3H,
). C NMR (100 MHz, DMSO-
): d 165.7, 151.9, 149.4, 141.9, 136.6, 135.1, 114.6, 112.4,
H
6. (a) Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem.
6
): d 10.42 (s, 1H, OH), 9.30 (s,
2000, 65, 3864–3868; (b) Wang, L.; Qian, C.; Tian, H.;
Ma, Y. Synth. Commun. 2003, 33, 1459–1468.
3
1
3
1
7. Sun, Q.; Wang, Y.; Ge, Z.; Cheng, T.; Li, R. Synthesis
3 3
OCH ), 2.28 (s, 3H, CH
2004, 1047–1051.
d
6
1
1
8. Lu, J.; Bai, Y. Synthesis 2002, 466–470.
9. Salehi, H.; Guo, Q.-X. Synth. Commun. 2004, 34, 171–
98.0, 56.4, 53.0, 50.9, 17.9. IR (KBr): 3353, 3213, 3089,
À1
2951, 2844, 1681, 1649, 1548 cm . MS (ESI): m/z 337.5
À
1
79.
0. Bose, D. S.; Fatima, L.; Mereyala, H. B. J. Org. Chem.
003, 68, 587–590.
(M ). Anal. Calcd for C14
H
15
3
N O
7
: C, 49.86; H, 4.48; N;
2
2
2
12.46. Found: C, 49.90; H, 4.36; N; 12.51.
Methyl 4-(3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetra-
2
1
1. Kidwai, M.; Saxena, S.; Mohan, R.; Venkataramanana,
R. J. Chem. Soc., Perkin Trans. 1 2002, 1845–1846.
2. (a) Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori,
G. Tetrahedron Lett. 1999, 40, 3465–3468; (b) Yadav, J. S.;
Reddy, B. V. S.; Srinivas, R.; Venugopal, C.; Ramalin-
gam, T. Synthesis 2001, 1341–1345; (c) Peng, J.; Deng, Y.
Tetrahedron Lett. 2001, 42, 5917–5919.
hydropyrimidine-5-carboxylate (4r): H NMR (400 MHz,
6
DMSO-d ): d 9.23(s, 1H, NH), 7.76 (s, 1H, NH), 7.26–
7.22 (m, 1H, ArH), 6.83–6.78 (m, 3H, ArH), 5.13 (s, 1H,
CH), 3.73 (s, 3H, OCH ), 3.54 (s, 3H, OCH ), 2.25 (s, 3H,
3
3
1
3
CH
3
). C NMR (100 MHz, DMSO-d
6
): d 165.8, 159.3,
152.2, 148.8, 146.1, 129.6, 118.1, 112.4, 112.1, 98.8, 54.9,
53.6, 50.8, 17.8. IR (KBr): 3218, 3098, 3000, 2951, 2836,
À1
2
2
3. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W.-L.
Chem. Rev. 2002, 102, 2227–2302.
4. Sr(OTf)
1700, 1642, 1608, 1587 cm . MS (ESI): m/z 275.3
+
(MÀH ). Anal. Calcd for C14
16 2 4
H N O : C, 60.86; H,
2
was prepared from the corresponding SrO and
5.84; N; 10.14. Found: C, 60.71; H, 5.82; N; 10.23.
Ethyl 4-(4-(dimethylamino)phenyl)-6-methyl-2-thioxo-
1,2,3,4-tetrahydropyrimidine-5-carboxylate (4v): H NMR
(400 MHz, DMSO-d ): d 10.23(s, 1H, NH), 9.54 (s, 1H,
TfOH in water according to the following literature:
Forsberg, J. H.; Spaziano, V. T.; Balasubramanian, T. M.;
Liu, G. K.; Kinsley, S. A.; Duckworth, C. A.; Poteruca, J.
J.; Brown, P. S.; Miller, J. L. J. Org. Chem. 1987, 52,
1
6
NH), 7.01 (d, 2H, J = 8.4 Hz, ArH), 6.66 (d, 2H,
1
017–1021.
5. Chen, X.; Fan, Y.; Zhen, Y.; Shen, Y. Chem. Rev. 2003,
03, 1955–1978.
6. General procedures for one-pot preparation of 3,4-dihy-
dropyrimidiones or its derivatives 4 using Sr(OTf) as a
catalyst: A mixture of aldehyde (5 mmol), b-diketoester
J = 8.4 Hz, ArH), 5.05 (s, 1H, CH), 3.99 (q, 2H,
2
2
J = 6.8 Hz, OCH
2
CH
3
), 2.86 (s, 6H, N(CH
3 2
) ), 2.27 (s,
13
1
3H, CH ), 1.12 (t, 3H, J = 6.8 Hz, OCH
3
2
CH ). C NMR
3
(100 MHz, DMSO-d ): d 173.8, 165.3, 149.9, 144.3, 131.2,
6
2
127.1, 112.2, 101.2, 59.5, 53.5, 40.1, 17.1, 14.1. IR (KBr):
3327, 3169, 2986, 1671, 1650, 1616, 1580, 1524, 1466, 1364,
À1
+
(
5 mmol) and urea or thiourea (7.5 mmol) and Sr(OTf)
2
1322, 1188, 1099 cm . MS (ESI): m/z 320.1 (M+H ).
(
0.05 mmol) was heated at 70 ꢁC under stirring for 4 h.
Anal. Calcd for C H N O S: C, 60.21; H, 6.63; N; 13.16.
1
6
21
3
2
After cooling, the reaction mixture was poured into cold
water and stirred for 5 min. The solid was suction filtered,
washed with cold water (20 mL · 2), filtered and recrys-
tallized from ethyl acetate or ethanol to afford pure
product. Selected physical data for compounds:
Found: C, 60.28; H, 6.60; N; 13.18.
Ethyl 6-methyl-2-thioxo-4-p-tolyl-1,2,3,4-tetrahydropyrim-
1
idine-5-carboxylate (4x): H NMR (400 MHz, DMSO-d
6
):
d 10.30 (s, 1H, NH), 9.61 (s, 1H, NH), 7.12 (d, 2H,
J = 8.0 Hz, ArH), 6.90 (d, 2H, J = 8.0 Hz, ArH), 5.12 (s,
Methyl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-
1H, CH), 4.00 (q, 2H, J = 6.8 Hz, OCH
2 3
CH ), 3.72 (s, 3H,
1
1,2,3,4-tetrahydropyrimidine-5-carboxylate (4o): H NMR
CH ), 2.29 (s, 3H, CH ), 1.11 (t, 3H, J = 6.8 Hz,
3
3
1
3
(
400 MHz, DMSO-d ): d 9.14 (s, 1H, NH), 8.91 (s, 1H,
OCH CH ). C NMR (100 MHz, DMSO-d ): d 174.0,
2 3 6
6
OH), 7.64 (s, 1H, NH), 6.81 (s, 1H, ArH), 6.69 (d, 2H,
165.1, 158.7, 144.7, 135.7, 127.6, 113.9, 100.9, 59.5, 55.0,
J = 8.0 Hz, ArH), 6.59 (d, 1H, J = 8.0 Hz, ArH), 5.06 (s,
53.4, 17.1, 14.0. IR (KBr): 3313, 3171, 3106, 2985, 1667,
À1
1
H, CH), 3.73 (s, 3H, OCH ), 3.54 (s, 3H, OCH ), 2.24 (s,
1610, 1575, 1509, 1461, 1371 cm
.
3
3