208
D.-H. Kweon, H.-K. Kim, J.-J. Kim, H. A Chung, W. S. Lee, S.-K. Kim and Y.-J. Yoon
Vol. 39
21.5, 45.7, 105.2, 129.3, 130.1, 133.2, 134.0, 145.8, 146.3, 156.0.
Anal. Calcd for C ClN O S: C, 50.63; H, 5.10; N, 11.81;
Anal. Calcd for C H ClN O S: C, 40.17; H, 3.09; N, 15.62;
12 11 4 5
S, 8.94. Found: C, 40.21; H, 3.12; N, 15.54; S, 8.87.
H
15 18
3 3
S, 9.01. Found: C, 50.77; H, 5.28; N, 11.78; S, 9.12.
Compound 4m has mp 163-164°; R = 0.18 (ethyl acetate/n-
f
Compound 4g has mp 164-166°; R = 0.25 (ethyl acetate/n-
hexane = 1:2, v/v); ir (potassium bromide): 3130, 3000, 2950,
2890, 1665, 1620, 1545, 1480, 1390, 1360, 1320, 1280, 1245,
f
hexane = 1:2, v/v);ir (potassium bromide): 3420, 2960, 2880,
1690, 1640, 1610, 1560, 1465, 1395, 1205, 1190, 1125, 1105,
-1
1
1200, 1100, 1060, 865, 820 cm ; H nmr (DMSO-d ): δ 1.20 (t,
6
-1
1
1050, 960, 835, 740 cm ; H nmr (DMSO-d ): δ 1.07 (m, 1H),
6H, J = 7.0, 7.0), 3.60 (t, 4H, J = 7.0), 8.17 (s, 1H), 8.28 (d, 2H,
6
13
1.37 (m, 4H), 1.59 (d, 1H, J = 13.0), 1.70 (d, 2H, J = 13.0), 1.80
(d, 2H, J = 11.0), 2.40 (s, 3H), 3.71 (m, 1H), 6.78 (d, NH, J = 8.0,
J = 8.8), 8.46 (d, 2H, J = 7.1); C nmr (DMSO-d ): δ 14.5, 45.8,
6
104.5, 124.9, 130.9, 134.2, 142.2, 145.9, 151.3, 155.9.
D O exchangeable), 7.46 (d, 2H, J = 8.0), 7.87 (d, 2H, J = 8.5),
Anal. Calcd for C H ClN O S: C, 43.47; H, 3.91; N, 14.48;
S, 8.29. Found: C, 43.51; H, 3.88; N, 14.51; S, 8.34.
2
14 15 4 5
13
8.23 (s, 1H); C nmr (DMSO-d ): δ 21.8, 24.4, 25.1, 33.8, 52.1,
6
106.3, 127.7, 129.6, 129.9, 133.8, 143.4, 146.0, 155.2.
Compound 4n has mp 216-217°; R = 0.30 (ethyl acetate/n-
f
Anal. Calcd for C
S, 8.40. Found: C, 53.52; H, 5.40; N, 11.22; S, 8.45.
Compound 4h has mp 183-185°; R = 0.48 (ethyl acetate/n-
H
ClN O S: C, 53.47; H, 5.28; N, 11.00;
hexane = 1:1, v/v); ir (potassium bromide): 3365, 3102, 2987, 2942,
2892, 1660, 1622, 1548, 1440, 1378, 1361, 1328, 1186, 11500,
17 20
3 3
-1
1
1125, 1095 cm ; H nmr (DMSO-d ): δ 1.27 (t, 3H, J = 7.2), 3.53
f
6
hexane = 1:2, v/v); ir (potassium bromide): 3377, 3094, 2966,
2937, 2976, 1666, 1622, 1538, 1470, 1438, 1384, 1326, 1276,
1191, 1147, 1090, 1030, 1009 cm ; H nmr (deuteriochloro-
(m, 2H), 7.08 (bs, NH, D O exchangeable), 7.94 (m, 3H), 8.11 (s,
2
13
1H), 8.45 (d, 1H, J = 0.6); C nmr (DMSO-d ): δ 15.5, 37.8, 102.9,
6
-1
1
124.7, 130.3, 132.2, 134.5, 134.6, 136.0, 145.0, 147.9, 154.8.
form): δ 1.35 (t, 3H, J = 7.2), 3.46 (m, 2H), 4.97 (bs, NH, D O
Anal. Calcd for C H ClN O S: C, 40.17; H, 3.09; N, 15.62;
2
12 11 4 5
exchangeable), 7.51 (d, 2H, J = 8.8), 7.78 (s, 1H), 8.11 (d, 2H, J =
8.8); C nmr (deuteriochloroform): δ 15.3, 38.3, 106.3, 127.8,
S, 8.94. Found: C, 40.21; H, 3.13; N, 15.66; S, 9.02.
13
Compound 4o has mp 164-165°; R = 0.18 (ethyl acetate/n-
f
129.3, 131.3, 135.1, 141.7, 144.2, 155.2.
hexane = 1:2, v/v); ir (potassium bromide): 3100, 3000, 2950,
2900, 1660, 1610, 1540, 1500, 1480, 1460, 1390, 1350, 1310,
Anal. Calcd for C H Cl N O S: C, 41.39; H, 3.18; N, 12.07;
12 11
2 3 3
-1
1
S, 9.21. Found: C, 41.52; H, 3.38; N, 12.22; S, 9.32.
1270, 1190, 1150, 1130, 1090 cm ; H nmr (DMSO-d ): δ 1.21
6
Compound 4i has mp 170-172°; R = 0.21 (ethyl acetate/n-
(t, 6H, J = 7.0), 3.63 (m, 4H), 8.07 (m, 2H), 8.10 (d, 1H, J = 7.8),
f
13
hexane = 1:2, v/v); ir (potassium bromide): 3092, 2982, 2964,
2934, 2871, 1644, 1604, 1529, 1497, 1468, 1393, 1350, 1317,
8.22 (s, 1H), 8.36 (d, 1H, J = 7.8); C nmr (DMSO-d ): δ 14.5,
6
46.0, 104.3, 125.4, 129.8, 133.1, 133.5, 143.2, 137.0, 146.0,
147.9, 155.7.
-1
1
1270, 1257, 1196, 1081, 1067, 1007 cm ; H nmr (deuteriochlo-
roform): δ 1.27 (t, 6H, J = 3.3), 3.56 (m, 4H), 7.51 (d, 2H, J =
8.8), 7.73 (s, 1H), 8.12 (d, 2H, J = 8.8); C nmr (deuteriochloro-
Anal. Calcd for C H ClN O S: C, 43.47; H, 3.91; N, 14.48;
S, 8.29. Found: C, 43.51; H, 3.98; N, 14.52; S, 8.32.
14 15 4 5
13
form): δ 13.3, 45.8, 108.3, 129.3, 131.4, 131.8, 135.1, 141.6,
Compound 4p has mp 204-205°; R = 0.15 (ethyl acetate/n-
f
145.6, 156.3.
Anal. Calcd for C
S, 8.52. Found: C, 44.73; H, 4.12; N, 11.22; S, 8.65.
hexane = 1:2, v/v); ir (potassium bromide): 3380, 3100, 3082,
2931, 2860, 1655, 1618, 1538, 1432, 1380, 1358, 1312, 1183,
H Cl N O S: C, 44.69; H, 4.02; N, 11.17;
14 15 2 3 3
-1
1
1123, 1107, 1030, 959, 821 cm ; H nmr (DMSO-d ): δ 1.09 (m,
6
Compound 4j has mp 180-182°; R = 0.61 (ethyl acetate/n-
1H), 1.40 (m, 4H), 1.60 (d, 1H, J = 13.0), 1.72 (d, 2H, J = 13.0),
f
hexane = 1:2, v/v); ir (potassium bromide): 3400, 3100, 2950,
2870, 1680, 1635, 1595, 1550, 1480, 1445, 1400, 1380, 1340,
1.83 (d, 2H, J = 10.0), 3.79 (m, 1H), 6.99 (bs, NH, D O
2
exchangeable), 8.05 (m, 3H), 8.35 (d, 1H, J = 7.5), 8.37 (s, 1H);
-1
1
13
1290, 1180, 1100, 1020, 1070 cm ; H nmr (DMSO-d ): δ 1.08
C nmr (DMSO-d ): δ 24.9, 25.2, 33.1, 52.3, 102.1, 125.4,
6
6
(m, 1H), 1.36 (m, 4H), 1.58 (d, 1H, J = 13.0), 1.69 (d, 2H, J =
13.5), 1.80 (d, 2H, J = 10.5), 3.72 (m, 1H), 6.84 (d, NH, J = 8.0,
130.8, 133.1, 134.2, 137.0, 144.8, 147.9, 154.9.
Anal. Calcd for C
H ClN O S: C, 46.55; H, 4.15; N, 13.57;
16 17 4 5
D O exchangeable), 7.73 (d, 2H, J = 9.0), 7.99 (d, 2H, J = 8.5),
8.26 (s, 1H); C nmr (deuteriochloroform): δ 24.4, 25.1, 33.8,
S, 7.77. Found: C, 46.61; H, 4.21; N, 13.62; S, 7.82.
2
13
Compound 4q has mp 178-180°; R = 0.19 (ethyl acetate/n-
f
52.1, 106.2, 128.1, 129.3, 131.3, 135.2, 141.6, 143.5, 155.2.
hexane = 1:2, v/v); ir (potassium bromide): 3093, 3017, 2940,
2859, 1646, 1605, 1539, 1446, 1377, 1356, 1292, 1280, 1181,
Anal. Calcd for C
H Cl N O S: C, 47.77; H, 4.26; N, 10.45;
16 17 2 3 3
-1
1
1123, 1088, 999 cm ; H nmr (deuteriochloroform): δ 1.75 (m,
S, 7.97. Found: C, 47.79; H, 4.29; N, 10.52; S, 8.02.
13
6H), 3. 55 (m, 4H), 7.85 (m, 3H), 7.87 (s, 1H), 8.66 (m, 1H);
C
Compound 4k has mp 164-166°; R = 0.37 (ethyl acetate/n-
f
nmr (deuteriochloroform): δ 23.9, 26.2, 50.5, 111.4, 124.7, 131.2,
132.4, 132.9, 135.5, 135.8, 147.8, 148.3, 156.4.
hexane = 1:2, v/v); ir (potassium bromide): 3130, 3070, 3000,
2950, 2850, 1660, 1600, 1520, 1445, 1380, 1280, 1260, 1180,
1125, 1175, 1000, 940, 870, 755 cm ; H nmr (DMSO-d6): δ
-1
1
Anal. Calcd for C H ClN O S: C, 45.17; H, 3.79; N, 14.05;
15 15 4 5
1.61 (s, 6H), 3.50 (m, 4H), 7.76 (d, 2H, J = 8.5), 8.01 (d, 2H, J =
S, 8.04. Found: C, 45.21; H, 3.82; N, 14.10; S, 8.11.
13
8.5), 8.17 (s, 1H); C nmr (DMSO-d ): δ 23.2, 25.8, 49.7, 108.4,
Compound 4r has mp 200-202°; R = 0.21 (ethyl acetate/n-
6
f
129.5, 130.7, 134.5, 135.2, 140.1, 147.4, 155.4.
hexane = 1:1, v/v); ir (potassium bromide): 3374, 3097, 3071,
2979, 2929, 2234, 1658, 1619, 1542, 1473, 1446, 1375, 1331,
1277, 1189, 1131, 1105, 1089 cm ; H nmr (deuteriochloroform
Anal. Calcd for C
H Cl N O S: C, 46.40; H, 3.89; N, 10.82;
15 15 2 3 3
-1
1
S, 8.26. Found: C, 46.37; H, 3.92; N, 10.91; S, 8.28.
+ DMSO-d ): δ 1.28 (t, 3H, J = 7.2), 3.52 (m, 2H), 6.87 (bs, NH,
Compound 4l has mp 202-204°; R = 0.10 (methylene chlo-
6
f
D O exchangeable), 7.90 (m, 3H), 8.07 (s, 1H), 8.33 (d, 1H, J =
ride); ir (potassium bromide): 3310, 3114, 2980, 2936, 1656,
1622, 1529, 1435, 1347, 1326, 1193, 1104, 1008, 854, 742, 680,
2
13
8.0); C nmr (deuteriochloroform + DMSO-d ): δ 15.5, 37.9,
6
-1
1
103.3, 110.7, 114.7, 131.8, 131.9, 133.1, 134.5, 135.3, 139.4,
144.9, 155.1.
633 cm ; H nmr (DMSO-d ): δ 1.17 (t, 3H, J = 7.0, 6.9), 3.46
6
(m, 2H), 7.43 (bs, NH, D O exchangeable), 8.25 (d, 2H, J = 9.0),
2
8.28 (s, 1H), 8.44 (d, 2H, J = 9.0); 13C nmr (DMSO-d ): δ 15.5,
Anal. Calcd for C H ClN O S: C, 46.09; H, 3.27; N, 16.54;
6
13 11 4 3
37.3, 101.9, 124.4, 130.3, 130.7, 142.0, 144.9, 150.8, 154.5.
S, 9.47. Found: C, 46.14; H, 3.31; N, 16.48; S, 9.51.