Yield (2.96 g, 74%); m.p. 208-210 C; IR (KBr) cm-1, 3230 (NH), 3056 (NH), 2971 (CH); 1671 (CO).
1H-NMR (500 MHz, DMSO-d ): 2.71 (t, J = 8.1 Hz, 2H, CH ), 3.11 (t, J = 8.1 Hz, 2H, CH ), 7.13
δ
6
2
2
(dd, J = 7.3, 7.3 Hz, 1H, Ar-H), 7.27 (dd, J = 7.4, 7.4 Hz, 1H, Ar-H), 7.33 (dd, J = 7.9, 7.9 Hz, 2H,
Ar-H), 7.42 (dd, J = 7.9, 7.9 Hz, 2H, Ar-H), 7.47 (d, J = 7.7 Hz, 2H, Ar-H), 7.54 (d, J = 7.7, 2H, Ar-
H), 7.61 (d, J = 8.4 Hz, 2H, Ar-H), 7.78 (d, J = 8.4 Hz, 2H, Ar-H), 9.92 (s, 1H, NH), 9.99 (s, 1H, NH).
13C-NMR (125 MHz, DMSO-d ): 22.12, 27.43, (122.70, CH 2), (123.63, CH 2), 124.57, (124.82,
δ
6
CH 2), 126.07, (126.38, CH 2), (128.29, CH 2), (128.50, CH 2), 130.87, 139.30, 141.06,
141.44, 151.60, 165.30, 179.32. EI-MS: (m/z, %): 400.12 (M+, 100), 404.19 (M++1, 26.89). Elemental
analysis for C23H20N4OS (400.50), calcd.: C, 68.98; H, 5.03; N, 13.99. Found: C, 68.95; H, 5.00; N,
13.95.
1-(4-Nitrophenyl)-3-[4-(6-oxo-4,5-dihydropyridazin-3-yl)phenyl]thiourea (8c).
Yield (2.66 g, 72%); m.p. 200-202 C; IR (KBr) cm-1, 3447 (NH), 3212 (NH), 3100 (NH), 2950 (CH),
1645 (CO). 1H-NMR (500 MHz, DMSO-d ): 2.43 (t, J = 8.3 Hz, 2H, CH ), 2.93 (t, J = 8.3 Hz, 2H,
δ
6
2
CH2), 7.57 (d, J = 8.7 Hz, 2H, Ar-H), 7.73 (d, J = 8.7 Hz, 2H, Ar-H), 7.81 (d, J = 9.1 Hz, 2H, Ar-H),
8.19 (d, J = 9.1 Hz, 2H, Ar-H), 10.41 (s, 1H, NH), 10.46 (s, 1H, NH), 10.91 (s, 1H, NH). 13C-NMR
(100 MHz, DMSO-d ): 22.17, 26.53, (118.24, CH 2), (120.28, CH 2), 125.96, (126.89, CH 2),
δ
6
(129.13, CH 2), 129.91, 139.02, 141.09, 149.64, 152.72, 167.46. EI-MS: (m/z, %): 369.15 (M+, 100),
370.19 (M++1, 20.85). Elemental analysis for C17H15N5O3S (369.40), calcd.: C,55.28; H, 4.09; N,
18.96. Found: C, 55.33; H, 4.14; N, 18.95.
1-(4-Nitrophenyl)-3-[4-(6-oxo-1-phenyl-4,5-dihydropyridazin-3-yl)phenyl]thiourea (8d).
Yield (3.30 g, 74%); m.p. 213-215 C; IR (KBr) cm-1, 3333 (NH), 3207 (NH), 2987 (CH), 1631 (CO).
1H-NMR (500 MHz, DMSO-d ): 2.72 (t, J = 8.1 Hz, 2H, CH ), 3.12 (t, J = 8.1 Hz, 2H, CH ), 7.26
δ
6
2
2
(dd, J = 7.4, 7.4 Hz, 1H, Ar-H), 7.42 (dd, J = 7.9, 7.9 Hz, 2H, Ar-H), 7.53 (d, J = 8.8 Hz, 2H, Ar-H),
7.61 (d, J = 8.8 Hz, 2H, Ar-H), 7.81–7.84 (m, 4H, Ar-H), 8.19 (d, J = 9.2 Hz, 2H, Ar-H), 10.45 (s, 1H,
NH), 10.48 (s, 1H, NH). 13C-NMR (125 MHz, DMSO-d ): 22.17, 26.85, (119.98, CH 2), (119.25,
δ
6
CH 2), 124.49, (127.02, CH 2), 126.92, (128.10, CH 2), (128.21, CH 2), (128.48, CH 2),
131.25, 139.82, 141.98, 142.01, 148.60, 162.95, 178.98. EI-MS: (m/z, %): 445.18 (M+, 100), 446.19
(M++1, 27.81). Elemental analysis for C23H19N5O3S (445.50), calcd.: C,62.01; H, 4.30; N, 15.72.
Found: C, 62.05; H, 4.34; N, 15.75.
1-(4-Nitrophenyl)-3-[4-(6-oxo-4,5-dihydropyridazin-3-yl)phenyl]urea (8e).