H Ar); 6.30 (1H, s, CH); 5.91 (1H, s, CH). 13C NMR spectrum, ꢁ, ppm: 192.9; 168.8; 165.2; 153.4; 152.2; 146.5;
146.1; 140.1; 132.2; 131.2; 125.1; 125.0; 123.9; 123.8; 120.5; 116.3; 84.2; 61.2. Mass spectrum, m/z (Irel, %):
379 [M]+ (5), 352 (10), 297 (20), 296 (25), 135 (80), 121 (100), 93 (90), 65 (25). Found, %: C 57.29; H 3.13;
N 18.19. C18H13N5O5. Calculated, %: C 56.99; H 3.45; N 18.46.
7-(4-Hydroxyphenyl)-6-[(2-hydroxyphenyl)carbonyl]-6,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-
1
5(4H)-one (7c). Yellow powder; mp 207ꢀ209ꢁC. IR spectrum, ꢀ, cm–1: 3407, 3076, 1661, 1608, 1562. H NMR
spectrum, ꢁ, ppm: 10.10 (2H, s, OH); 9.45 (1H, s, NH); 7.80–7.75 (1H, m, H Ar); 7.70 (1H, s, CH); 7.65–7.59
(2H, m, H Ar); 7.56–7.53 (1H, m, H Ar); 7.15–7.10 (2H, m, H Ar); 7.10–7.03 (2H, m, H Ar); 6.32 (1H, s, CH);
6.01 (1H, s, CH). 13C NMR spectrum, ꢁ, ppm: 192.1; 169.0; 165.6; 153.0; 152.1; 150.1; 141.0; 132.4; 131.4;
124.8; 124.0; 122.8; 121.9; 117.1; 85.2; 59.9. Mass spectrum, m/z (Irel, %): 350 [M]+ (5), 323 (10), 268 (15), 267
(20), 135 (80), 121 (100), 51 (17). Found, %: C 62.00; H 4.22; N 15.61. C18H14N4O4. Calculated, %: C 61.71;
H 4.03; N 15.99.
6-[(2-Hydroxyphenyl)carbonyl]-7-phenyl-6,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (7d).
White powder; mp 217ꢀ219ꢁC. IR spectrum, ꢀ, cm–1: 3394, 3264, 1684, 1598, 1569. 1H NMR spectrum, ꢁ, ppm:
10.10 (1H, s, OH); 9.45 (1H, s, NH); 7.61 (1H, s, CH); 7.35–7.31 (2H, m, H Ar); 7.25–7.21 (2H, m, H Ar);
7.20–7.17 (2H, m, H Ar); 7.15–7.13 (1H, m, H Ar); 7.10–7.00 (2H, m, H Ar); 6.00 (1H, s, CH); 5.90 (1H, s,
13
CH). C NMR spectrum, ꢁ, ppm: 192.1; 168.8; 165.0; 153.5; 152.5; 140.2; 132.9; 132.4; 132.0; 124.5; 124.1;
122.9; 120.0; 117.2; 84.8; 61.2. Mass spectrum, m/z (Irel, %): 334 [M]+ (10), 307 (15), 252 (15), 251 (20), 135
(80), 121 (100), 51 (15). Found, %: C 64.39; H 4.11; N 16.81. C18H14N4O3. Calculated, %: C 64.66; H 4.22;
N 16.76.
7-(4-Chlorophenyl)-6-[(2-hydroxyphenyl)carbonyl]-6,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-
1
5(4H)-one (7e). Pale-yellow powder; mp 229ꢀ230ꢁC. IR spectrum, ꢀ, cm–1: 3241, 3081, 1670, 1603, 1564. H
NMR spectrum, ꢁ, ppm: 10.00 (1H, s, OH); 8.92 (1H, s, NH); 7.77 (1H, s, CH); 7.85–7.51 (2H, m, H Ar); 7.39–
7.33 (2H, m, H Ar); 7.32–7.29 (1H, m, H Ar); 7.21–7.10 (3H, m, H Ar); 6.21 (1H, s, CH); 5.95 (1H, s, CH). 13C
NMR spectrum, ꢁ, ppm: 193.0; 167.8; 166.1; 153.3; 151.9; 140.2; 133.0; 132.5; 131.8; 128.1; 126.4; 123.8;
123.1; 118.0; 84.5; 61.2. Mass spectrum, m/z (Irel, %): 368/370 [M]+ (5), 341 (10), 286 (20), 285 (25), 135 (85),
121 (100), 51 (20). Found, %: C 58.89; H 4.19; N 15.51. C18H13ClN4O3. Calculated, %: C 58.62; H 3.55;
N 15.19.
7-(2-Furyl)-6-[(2-hydroxyphenyl)carbonyl]-6,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (7f).
Gray powder; mp 250ꢀ251ꢁC. IR spectrum, ꢀ, cm–1: 3372, 3250, 3122, 1693. 1H NMR spectrum, ꢁ, ppm: 10.11
(1H, s, OH); 9.90 (1H, s, NH); 7.68 (1H, s, CH); 7.75–7.67 (1H, m, H Ar); 7.56–7.51 (1H, m, H Ar); 7.50–7.47
(1H, m, H Ar); 7.43–7.38 (1H, m, H Ar); 7.13–7.05 (2H, m, H Ar); 6.90–6.88 (1H, m, H Ar); 6.22 (1H, s, CH);
6.01(1H, s, CH). 13C NMR spectrum, ꢁ, ppm: 192.8; 168.9; 166.8; 154.4; 152.7; 149.2; 135.6; 133.0; 132.5;
124.1; 122.4; 121.8; 119.3; 118.0; 85.1; 62.2. Mass spectrum, m/z (Irel, %): 324 [M]+ (10), 242 (15), 241 (20),
135 (80), 121 (100), 51 (20). Found, %: C 58.99; H 4.05; N 17.76. C16H12N4O4. Calculated, %: C 59.26; H 3.73;
N 17.28.
6-[(2-Hydroxyphenyl)carbonyl]-5-(4-nitrophenyl)-5,8-dihydropyrido[2,3-d]pyrimidine-2,4,7(1H,3H,6H)-
trione (8a). Yellow powder; mp > 300°C. IR spectrum, ꢀ, cm–1: 3405, 3345, 3178, 1718, 1627, 1518, 1460,
1394. 1H NMR spectrum, ꢁ, ppm: 10.68 (1H, s, NH); 10.49 (1H, s, NH); 10.16 (1H, s, NH); 10.14 (1H, s, OH);
8.20–8.17 (2H, m, H Ar); 8.15–8.10 (2H, m, H Ar); 7.54–7.51 (2H, m, H Ar); 7.45–7.42 (2H, m, H Ar); 6.26
13
(1H, s, CH); 4.50 (1H, s, CH). C NMR spectrum, ꢁ, ppm: 191.0; 165.1; 164.3; 164.0; 156.0; 151.8; 150.6;
149.7; 146.1; 142.4; 130.3; 128.8; 124.5; 120.4; 119.7; 109.1; 75.0; 33.9. Mass spectrum, m/z (Irel, %): 422 [M]+
(5), 336 (17), 297 (22), 269 (34), 121 (65), 86 (100). Found, %: C 57.09; H 3.48; N 13.38. C20H14N4O7.
Calculated, %: C 56.88; H 3.34; N 13.27.
6-[(2-Hydroxyphenyl)carbonyl]-5-(3-nitrophenyl)-5,8-dihydropyrido[2,3-d]pyrimidine-2,4,7(1H,3H,6H)-
trione (8b). Yellow powder; mp > 300°C. IR spectrum, ꢀ, cm–1: 3405, 3346, 3180, 1710, 1628, 1465, 1396. 1H
NMR spectrum, ꢁ, ppm: 10.80 (1H, s, NH); 10.51 (1H, s, NH); 10.20 (1H, s, NH); 10.14 (1H, s, OH); 8.40–8.33
(1H, m, H Ar); 8.20–8.00 (2H, m, H Ar); 7.74–7.72 (1H, m, H Ar); 7.70–7.68 (2H, m, H Ar); 7.55–7.52 (1H, m,
742
ꢀ