Journal of the Iranian Chemical Society
151.48, 137.78, 137.06, 136.62, 134.97, 129.93, 129.55,
129.05, 126.94, 87.31, 68.18, 35.12, 21.02.
brown powder, yield: 91%, m.p. >300 °C; IR (KBr) (ν,
cm−1): 3352, 3224, 3128, 2925, 2853, 1683, 1668, 1619,
1563, 1525, 1445, 1139, 782; 1H NMR (301 MHz, DMSO-
d6) (δ, ppm): 10.54 (s, 1H), 10.44 (s, 1H), 8.60 (s, 1H), 8.11
(s, 1H), 7.76 (d, J= 7.6 Hz, 3H), 7.61 (t, J= 7.8 Hz, 2H),
7.21 (d, J=8.1 Hz, 2H), 6.94 (d, J=8.1 Hz, 2H), 4.35 (d,
J=8.1 Hz, 2H), 2.44 (s, 3H). 13C NMR (76 MHz, DMSO)
(δ, ppm): 163.26, 159.15, 155.04, 151.42, 137.71, 137.38,
136.59, 135.00, 129.56, 129.06, 127.68, 127.00, 87.07,
67.96, 35.04, 15.22.
7-Amino-5-(2,6-dichlorophenyl)-6-(phenylsulfonyl)-6,
8a-dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
(4e) White powder, yield: 92%, m.p. >300 °C; IR (KBr)
(ν, cm−1): 3321, 3073, 2993, 2819, 1699, 1642, 1611, 1548,
1518, 1465, 758; 1H NMR (301 MHz, DMSO-d6) (δ, ppm):
10.50 (s, 1H), 10.32 (s, 1H), 8.68 (s, 1H), 8.03 (s, 1H), 7.80
(dd, J=20.7, 7.4 Hz, 3H), 7.63 (t, J=7.6 Hz, 2H), 7.47 (d,
J=7.3 Hz, 1H), 7.30 (dt, J=15.7, 7.6 Hz, 2H), 5.28 (s, 1H),
4.42 (s, 1H); 13C NMR (76 MHz, DMSO) (δ, ppm): 163.11,
160.17, 155.75, 151.44, 136.57, 136.41, 136.26, 135.15,
134.94, 130.53, 129.98, 129.69, 129.40, 84.73, 65.74, 33.13.
7-Amino-5-(2-chlorophenyl)-6-(phenylsulfonyl)-6,8a-dihy-
dropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4j) White
powder, yield: 92%, m.p. >300 °C; IR (KBr) (ν, cm−1):
3321, 3073, 2993, 2933, 2819, 1698, 1642, 1612, 1548,
1517, 758; 1H NMR (301 MHz, DMSO-d6) (δ, ppm): 10.71
(s, 1H), 10.56 (s, 1H), 8.58 (s, 1H), 8.12 (s, 1H), 7.79 (dd,
J = 7.8, 5.2 Hz, 3H), 7.64 (t, J = 7.7 Hz, 2H), 7.48 (dd,
J=7.6, 1.6 Hz, 1H), 7.36–7.18 (m, 2H), 6.84 (dd, J=7.5,
2.0 Hz, 1H), 4.82 (s, 1H), 4.34 (s, 1H); 13C NMR (76 MHz,
DMSO) (δ, ppm): 163.16, 159.06, 156.47, 151.48, 136.91,
136.63, 135.01, 132.73, 130.46, 129.85, 129.61, 129.34,
128.91, 128.18, 86.01, 65.97, 32.76.
7-Amino-5-(4-methoxyphenyl)-6-(phenylsulfonyl)-6,8a-
dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4f) Light
gray powder, yield: 91%, m.p. >300 °C; IR (KBr) (ν, cm−1):
3401, 3091, 2928, 1697, 1651, 1512, 1447, 1311, 1175; 1H
NMR (301 MHz, DMSO-d6) (δ, ppm): 10.50 (s, 1H), 10.40
(s, 1H), 8.59–8.51 (m, 1H), 8.10 (s, 1H), 7.76 (d, J=7.7 Hz,
3H), 7.61 (t, J = 7.7 Hz, 2H), 6.96–6.82 (m, 4H), 4.33 (d,
J=11.5 Hz, 2H), 3.71 (s, 3H); 13C NMR (76 MHz, DMSO)
(δ, ppm): 163.27, 159.13, 158.96, 154.92, 151.40, 136.65,
134.94, 132.65, 129.54, 129.04, 128.14, 114.78, 87.49,
68.24, 55.58, 34.73.
7-Amino-5-(4-chlorophenyl)-6-(phenylsulfonyl)-6,8a-dihy-
dropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4 k) White
powder, yield: 93%, m.p. >300 °C; IR (KBr) (ν, cm−1):
3373, 3124, 2926, 2853, 1668, 1620, 1569, 1523, 1490, 813;
1H NMR (301 MHz, DMSO-d6) (δ, ppm): 10.55 (s, 1H),
10.45 (s, 1H), 8.61 (s, 1H), 8.09 (s, 1H), 7.76 (d, J=7.8 Hz,
3H), 7.61 (t, J=7.7 Hz, 2H), 7.39 (d, J=8.0 Hz, 2H), 7.03
(d, J = 8.1 Hz, 2H), 4.39 (d, J = 11.0 Hz, 2H); 13C NMR
(76 MHz, DMSO) (δ, ppm): 163.24, 159.07, 155.20, 151.36,
139.76, 136.52, 135.04, 132.46, 129.58, 129.40, 129.07,
129.02, 86.73, 67.74, 35.00.
7-Amino-6-(phenylsulfonyl)-5-(thiophen-2-yl)-6,8a-dihydro
pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4 g) Gray pow-
der, yield: 90%, m.p. >300 °C; IR (KBr) (ν, cm−1): 3371,
3130, 2933, 2851, 1688, 1668, 1621, 1558, 1519, 1447; 1H
NMR (301 MHz, DMSO-d6) (δ, ppm): 10.48 (s, 2H), 8.67
(s, 1H), 8.28 (s, 1H), 7.82–7.69 (m, 3H), 7.59 (dd, J =8.4,
7.1 Hz, 2H), 7.36 (dd, J=5.1, 1.2 Hz, 1H), 6.94 (dd, J=5.1,
3.5 Hz, 1H), 6.81 (d, J=3.5 Hz, 1H), 4.67 (s, 1H), 4.54; 13
C
NMR (76 MHz, DMSO) (δ, ppm): 163.03, 159.34, 154.58,
151.24, 144.68, 136.51, 135.05, 129.55, 129.01, 127.60,
125.58, 124.50, 88.12, 67.70, 31.19.
7-Amino-5-(2-nitrophenyl)-6-(phenylsulfonyl)-6,8a-dihydro
pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4 l) Light green
powder, yield: 94%, m.p. >300 °C; IR (KBr) (ν, cm−1):
3410, 3324, 3094, 3000, 2867, 2812, 1712, 1645, 1620,
1563, 1503, 1453, 1426, 1332, 1076; 1H NMR (301 MHz,
DMSO-d6) (δ, ppm): 10.70–10.63 (m, 1H), 10.58–10.50 (m,
1H), 8.66 (s, 1H), 8.14 (s, 1H), 8.00 (dd, J=8.0, 1.4 Hz, 1H),
7.86–7.70 (m, 3H), 7.71–7.48 (m, 4H), 7.04 (dd, J = 7.9,
1.4 Hz, 1H), 4.97 (s, 1H), 4.56 (s, 1H); 13C NMR (76 MHz,
DMSO) (δ, ppm): 163.01, 159.86, 156.51, 151.45, 148.77,
137.10, 135.00, 134.47, 133.80, 129.71, 129.66, 129.53,
129.22, 125.30, 86.82, 66.92, 31.23.
7-Amino-5-(2-bromophenyl)-6-(phenylsulfonyl)-6,8a-dihydr
opyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4 h) Gray pow-
der, yield: 92%, m.p. >300 °C; IR (KBr) (ν, cm−1): 3406,
3091, 2926, 2853, 1704, 1642, 1552, 1514, 1552, 758; 1H
NMR (300 MHz, DMSO-d6) (δ, ppm): 10.68 (s, 1H), 10.54
(s, 1H), 8.55 (s, 1H), 8.12 (s, 1H), 7.79 (d, J=7.7 Hz, 3H),
7.63 (t, J=7.8 Hz, 3H), 7.25 (dt, J=23.7, 7.3 Hz, 2H), 6.82
(d, J=7.5 Hz, 1H), 4.82 (s, 1H), 4.34; 13C NMR (76 MHz,
DMSO) (δ, ppm): 163.11, 159.24, 156.47, 151.56, 138.05,
137.01, 135.01, 133.85, 130.17, 129.61, 129.40, 129.15,
128.74, 123.41, 86.58, 66.21, 35.15.
7-Amino-5-(4-nitrophenyl)-6-(phenylsulfonyl)-6,8a-dihydr
opyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4 m) Cloudy
white powder, yield: 95%, m.p. >300 °C; IR (KBr) (ν,
cm−1): 3444, 3393, 3214, 3081, 2925, 1725, 1699, 1682,
7-Amino-5-(4-(methylthio)phenyl)-6-(phenylsulfonyl)-6,8a-
dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4i) Light
1 3