840
S. Tu, X. Zhu, F. Shi, J. Zhang, Y. Zhang
Vol 44
5
Hz, ArH), 5.82 (d, 1H, J = 4.4 Hz, CH), 4.01ꢀ3.96 (m, 1H,
1
1031, 916, 800, 787, 698 cm-1; H nmr (DMSO-d6): ꢁ 9.87 (s,
1H, NH), 8.35 (s, 1H, ArH), 8.21 (dd, 1H, J1 = 8.0 Hz, J2 = 1.4
Hz, ArH), 8.03 (d, 1H, J = 8.4 Hz, ArH), 7.69 (t, 1H, J = 8.0 Hz,
ArH), 6.95-6.91 (m, 1H, ArH), 6.90 (s, 1H, ArH), 6.83 (dd, 1H,
3
4CH), 2.76 (dd, 1H, J1 = 16.0, J2 = 6.4 Hz, CH2), 2.51 (dd, 1H,
J1 = 16.0 Hz, J2 = 8.0 Hz, 3CH2). Anal. Calcd. for C17H13BrN2O3:
C, 54.71; H, 3.51; N, 7.51. Found: C, 54.62; H, 3.43; N, 7.41.
4-(2-Chlorophenyl)-6-(3-nitrophenyl)-3,4-dihydropyridin-
2 (1H)-one (5c). ir (potassium bromide): 3188, 3072, 2921,
1695, 1618, 1577, 1528, 1474, 1411, 1349, 1258, 1162, 1041,
5
J1 = 8.4 Hz, J2 = 2.0 Hz, ArH), 5.79 (d, 1H, J = 4.4 Hz, CH),
3.96ꢀ3.87 (m, 1H, 4CH), 3.75 (s, 3H, OCH3), 3.73 (s, 3H,
OCH3), 2.72 (dd, 1H, J1 = 15.8 Hz, J2 = 7.0 Hz, 3CH2), 2.58 (dd,
1H, J1 = 15.8 Hz, J2 = 8.8 Hz, 3CH2). Anal. Calcd. for
C19H18N2O5: C, 64.40; H, 5.12; N, 7.91. Found: C, 64.51; H,
5.09; N, 7.85.
1
809, 790, 740 cm-1; H nmr (DMSO-d6): ꢁ 10.01 (s, 1H, NH),
8.38 (s, 1H, ArH), 8.23 (d, 1H, J = 8.0 Hz, ArH), 8.04 (d, 1H, J
= 8.0 Hz, ArH), 7.70 (t, 1H, J = 8.0 Hz, ArH), 7.51 (d, 1H, J =
7.8 Hz, ArH), 7.41ꢀ7.30 (m, 3H, ArH), 5.79 (d, 1H, J = 4.8 Hz,
5CH), 4.33ꢀ4.28 (m, 1H, 4CH), 2.84 (dd, 1H, J1 = 16.0, J2 = 7.2
4-(4-Methylphenyl)-6-(3-nitrophenyl)-3,4-dihydropyridin-
2(1H)-one (5i). ir (potassium bromide): 3234, 3125, 1682, 1651,
1611, 1530, 1471, 1349, 810, 781 cm-1; 1H nmr (DMSO-
d6): ꢁ 9.88 (s, 1H, NH), 8.35 (s, 1H, ArH), 8.21 (d, 1H, J = 8.4
Hz, ArH), 8.03 (d, 1H, J = 8.0 Hz, ArH), 7.68 (t, 1H, J = 7.6 Hz,
ArH), 7.21 (d, 2H, J = 7.2 Hz, ArH), 7.15 (d, 2H, J = 7.2 Hz,
3
Hz, CH2), 2.54 (dd, 1H, J1 = 15.6 Hz, J2 = 6.4 Hz, 3CH2). Anal.
Calcd. for C17H13ClN2O3: C, 62.11; H, 3.99; N, 8.52. Found: C,
62.24; H, 4.02; N, 8.56.
4-(2,4-Dichlorophenyl)-6-(3-nitrophenyl)-3,4-dihydropyri-
din-2(1H)-one (5d). ir (potassium bromide): 3228, 3107, 1682,
1625, 1530, 1463, 1342, 1254, 1094, 1041, 897, 805, 784, 696
5
4
ArH), 5.79 (d, 1H, J = 4.4 Hz, CH), 3.93ꢀ3.88 (m, 1H, CH),
2.74 (dd, 1H, J1 = 16.0 Hz, J2 = 5.4 Hz, 3CH2), 2.53 (dd, 1H, J1 =
1
cm-1; H nmr (DMSO-d6): ꢁ 10.06 (s, 1H, NH), 8.38 (s, 1H,
3
16.0 Hz, J2 = 6.4 Hz, CH2), 2.28 (s, 3H, CH3). Anal. Calcd. for
ArH), 8.24 (d, 1H, J = 8.0 Hz, ArH), 8.06 (d, 1H, J = 8.4 Hz,
ArH), 8.39 (t, 1H, J = 8.0 Hz, ArH), 8.05 (d, 1H, J = 8.0 Hz,
C18H16N2O3: C, 70.12; H, 5.23; N, 9.09. Found: C, 70.26; H,
5.14; N, 9.01.
5
ArH), 7.57ꢀ7.39 (m, 2H, ArH), 5.82 (d, 1H, J = 4.4 Hz, CH),
4-(3,4-Methylenedioxylphenyl)-6-(3-nitrophenyl)-3,4-
dihydropyridin-2(1H)-one (5j). ir (potassium bromide): 3199,
3095, 2890, 1668, 1608, 1520, 1440, 1344, 1242, 1039, 937,
806, 792 cm-1; 1H nmr (DMSO-d6): ꢁ 9.87 (s, 1H, NH), 8.35 (s,
1H, ArH), 8.21 (d, 1H, J = 8.4 Hz, ArH), 8.02 (d, 1H, J = 8.0
Hz, ArH), 7.71 (t, 1H, J = 8.0 Hz, ArH), 6.92ꢀ6.86 (m, 2H,
ArH), 6.78 (d, 1H, J = 8.0 Hz, ArH), 5.98 (s, 2H, OCH2O), 5.78
(d, 1H, J = 4.8 Hz, 5CH), 3.94ꢀ3.86 (m, 1H, 4CH), 2.68 (dd, 1H,
J1 = 16.0 Hz, J2 = 6.8 Hz, 3CH2), 2.51 (dd, 1H, J1 = 15.8 Hz, J2 =
4
4.33ꢀ4.28 (m, 1H, CH), 2.82 (dd, 1H, J1 = 16.0, J2 = 7.2 Hz,
3
3CH2), 2.58 (dd, 1H, J1 = 15.8 Hz, J2 = 8.0 Hz, CH2). Anal.
Calcd. for C17H12Cl2N2O3: C, 56.22; H, 3.33; N, 7.71. Found: C,
56.33; H, 3.18; N, 7.78.
4-(3,4-Dichlorophenyl)-6-(3-nitrophenyl)-3,4-dihydropyri-
din-2(1H)-one (5e). ir (potassium bromide): 3231, 3099, 1695,
1630, 1521, 1465, 1353, 1285, 1138, 1030, 971, 927, 810, 787
cm-1; 1H nmr (DMSO-d6): ꢁ 9.96 (s, 1H, NH), 8.37 (s, 1H,
ArH), 8.22 (dd, 1H, J1 = 8.4 Hz, J2 = 1.2 Hz, ArH), 8.04 (d, 1H,
J = 8.4 Hz, ArH), 7.69 (t, 1H, J = 8.0 Hz, ArH), 7.63 (s, 1H,
ArH), 7.61 (d, 1H, J = 8.0 Hz, ArH), 7.35 (dd, 1H, J1 = 8.4 Hz,
J2 = 2.0 Hz, ArH), 5.81 (d, 1H, J = 4.0 Hz, 5CH), 4.06ꢀ4.01 (m,
3
8.0 Hz, CH2). Anal. Calcd. for C18H14N2O5: C, 63.90; H, 4.17;
N, 8.28. Found: C, 64.01; H, 4.12; N, 8.33.
4-Butyl-6-(3-nitrophenyl)-3,4-dihydropyridin-2(1H)-one
(5k). ir (potassium bromide): 3231, 3098, 2950, 2892, 1681,
1625, 1522, 1467, 1352, 1105, 812, 791, 709 cm-1; 1H nmr
(DMSO-d6): ꢁ 9.70 (s, 1H, NH), 8.29 (s, 1H, ArH), 8.18 (d, 1H,
J = 8.0 Hz, ArH), 7.97 (d, 1H, J = 8.0 Hz, ArH), 7.67 (t, 1H, J =
4
3
1H, CH), 2.77 (dd, 1H, J1 = 16.6 Hz, J2 = 7.4 Hz, CH2), 2.60
3
(dd, 1H, J1 = 15.8 Hz, J2 = 8.8 Hz, CH2). Anal. Calcd. for
C17H12Cl2N2O3: C, 56.22; H, 3.33; N, 7.71. Found: C, 56.26; H,
3.36; N, 7.76.
5
8.0 Hz, ArH), 5.64 (d, 1H, J = 3.6 Hz, CH), 2.59ꢀ2.55 (m, 1H,
3
4CH), 2.48 (dd, 1H, J1 = 17.0 Hz, J2 = 7.4 Hz, CH2), 2.21 (dd,
4-(4-Flurophenyl)-6-(3-nitrophenyl)-3,4-dihydropyridin-
2(1H)-one (5f). ir (potassium bromide): 3233, 3124, 1685, 1648,
1530, 1469, 1352, 1218, 1162, 827, 775, 693 cm-1; 1H nmr
(DMSO-d6): ꢁ 9.94 (s, 1H, NH), 8.37 (s, 1H, ArH), 8.22 (d, 1H,
J = 8.0 Hz, ArH), 8.04 (d, 1H, J = 7.2 Hz, ArH), 7.69 (t, 1H, J =
7.8 Hz, ArH), 7.39ꢀ7.35 (m, 2H, ArH), 7.21ꢀ7.16 (m, 2H, ArH),
5.81 (d, 1H, J = 4.4 Hz, 5CH), 4.02ꢀ3.98 (m, 1H, 4CH), 2.76 (dd,
1H, J1 = 15.6, J2 = 6.8 Hz, 3CH2), 2.56 (dd, 1H, J1 = 15.6 Hz, J2 =
3
1H, J1 = 15.6 Hz, J2 = 9.2 Hz, CH2), 1.46ꢀ1.33 (m, 6H, 3 ꢀ
CH2), 0.91 (t, 3H, J = 7.0 Hz, CH3). Anal. Calcd. for
C15H18N2O3: C, 65.68; H, 6.61; N, 10.21. Found: C, 65.79; H,
6.52; N, 10.13.
4-(2-Thiofuran)-6-(3-nitrophenyl)-3,4-dihydropyridin-
2(1H)-one (5l). ir (potassium bromide): 3215, 3089, 1697, 1654,
1
1524, 1471, 1416, 1349, 1282, 1050, 798, 700 cm-1; H nmr
3
8.4 Hz, CH2). Anal. Calcd. for C17H13FN2O3: C, 65.38; H, 4.20;
N, 8.97. Found: C, 65.45; H, 4.32; N, 8.78.
(DMSO-d6): ꢁ 9.94 (s, 1H, NH), 8.35 (s, 1H, ArH), 8.23 (d, 1H,
J = 7.6 Hz, ArH), 8.03 (d, 1H, J = 8.0 Hz, ArH), 7.70 (t, 1H, J =
8.0 Hz, ArH), 7.40 (dd, 1H, J1 = 5.0 Hz, J2 = 1.0 Hz, thiophen-2-
yl-H), 7.01ꢀ6.99 (m, 2H, thiophen-2-yl-H), 5.87 (d, 1H, J = 4.8
4-(3-Nitrophenyl)-6-(3-nitrophenyl)-3,4-dihydropyridin-
2(1H)-one (5g). ir (potassium bromide): 3230, 3081, 1686,
1
1643, 1577, 1521, 1352, 1102, 805, 790 cm-1; H nmr (DMSO-
5
4
Hz, CH), 4.28ꢀ4.21 (m, 1H, CH), 2.87 (dd, 1H, J1 = 16.0 Hz,
3
d6): ꢁ 10.03 (s, 1H, NH), 8.39 (s, 1H, ArH), 8.23 (dd, 1H, J1 =
8.0 Hz, J2 = 1.6 Hz, ArH), 8.20 (s, 1H, ArH), 8.14 (dd, 1H, J1 =
8.0 Hz, J2 = 1.6 Hz, ArH), 8.05 (d, 1H, J = 8.0 Hz, ArH), 7.84
(d, 1H, J = 7.6 Hz, ArH), 7.73ꢀ7.65 (m, 2H, ArH), 5.87 (d, 1H,
J2 = 6.8 Hz, CH2), 2.61 (dd, 1H, J1 = 15.8 Hz, J2 = 6.8 Hz,
3CH2). Anal. Calcd. for C15H12N2O3S: C, 59.99; H, 4.03; N, 9.33;
S, 10.68. Found: C, 60.08; H, 3.96; N, 9.25; S, 10.62.
4-(4-Chlorophenyl)-6-(4-methoxyphenyl)-3,4-dihydro-
pyridin-2(1H)-one (5m). ir (potassium bromide): 3220, 3101,
5
4
J = 3.6 Hz, CH), 4.22ꢀ4.19 (m, 1H, CH), 2.83 (dd, 1H, J1 =
3
1
1671, 1652, 1609, 1518, 1472, 1373, 1245, 1190, 819 cm-1; H
16.0 Hz, J2 = 6.8 Hz, CH2), 2.66 (dd, 1H, J1 = 15.8 Hz, J2 = 8.8
Hz, CH2). Anal. Calcd. for C17H13N3O5: C, 60.18; H, 3.86; N,
12.38. Found: C, 60.34; H, 3.79; N, 12.45.
3
nmr (DMSO-d6): ꢁ 9.60 (s, 1H, NH), 7.49 (d, 1H, J = 8.8 Hz,
ArH), 7.39 (d, 1H, J = 8.4 Hz, ArH), 7.32 (d, 1H, J = 8.4 Hz,
ArH), 6.93 (d, 1H, J = 8.8 Hz, ArH), 5.44 (d, 1H, J = 4.4 Hz,
4-(3,4-Dimethoxyphenyl)-6-(3-nitrophenyl)-3,4-dihydro-
pyridin-2(1H)-one (5h). ir (potassium bromide): 3250, 3099,
2935, 2835, 1683, 1609, 1593, 1523, 1416, 1352, 1262, 1138,
4
5CH), 3.93ꢀ3.88 (m, 1H, CH), 3.76 (s, 3H, OCH3), 2.71 (dd,
1H, J1 = 16.0 Hz, J2 = 6.8 Hz, 3CH2), 2.48 (dd, 1H, J1 = 15.2 Hz,