Z. Esam et al.
2.3.4 (Z)‑5‑(2‑(4‑bromophenyl)‑2‑oxoethylidene)
imidazolidine‑2,4‑dione (2b)
DMSO-d6): δ (ppm) 12.60 (s, broad, 1H), 7.85 (s.1H), 7.68
(dd, 1H), 7.55 (dd, 1H), 7.38 (dt, 1H), 7.11 (dt, 1H) 7.04
(s, 1H, CH=), 3.88 (s,3H); 13C-NMR (100 MHz, DMSO-
d6): 34.17,101.09, 111.1, 119.23, 120.12, 121.19, 122.20,
125.80, 131.58, 135.10, 140.05, 166.36, 168.19; MS: (m/z,
%), 259 m/z (M+, 11), 232 (4), 206 (53), 187 (34), 182.9
(27), 143 (80), 162 (6), 127 (28), 114 (24),76 (55), 74.1 (66),
59.01 (100); Elemental anal. (%), calced for C13H10N2O2S:C,
60.54; H, 3.90; N, 10.85; found: C, 59.06; H, 3.25; N, 10.29.
IR (KBr, vmax, cm−1): 3420 (NH), 1741 (N–C=O),
1189(N–C=S), 1581 (C=C), 841 (C–Br), 2829 (CH–Ar)
1
cm−1; H NMR (400 MHz, DMSO-d6): δ (ppm): 6.97 (s,
1H,=CH), 7. 93 (d, J=8.8 Hz, 2H, ArH), 8.17(d, J=8.8 Hz,
2H, ArH) 7.90 (1H, NH), 12.90 (brs, 1H, NH); 13C-NMR
(100 MHz, DMSO-d6): ppm 131.35, 129.54, 134.57, 138.60,
144.44, 148.48, 181.51, 188.56, 189.97, 198.64; MS: (m/z,
%) 295. (M+, 10); 279 (7), 207 (60), 188 (32), 182 (22), 171
(40), 154 (37), 143 (75), 110 (27), 85 (57),55(100); Elemen-
tal anal. (%), calced for C11H7BrN2O3: C, 44.77; H, 2.39; N,
9.49; found: C, 40.36; H, 1.73; N, 4.24.
2.3.8 (Z)‑5‑((1‑methyl‑1H‑indol‑2‑yl)methylene)
imidazolidine‑2,4‑dione (4b)
IR (KBr): νmax3430 (N–H), 1765 (N–C=O), 1699
(N–C=O) cm−1 1H-NMR (400 MHz, DMSO-d6): δ
;
2.3.5 (Z)‑5‑(2‑(4‑methoxyphenyl)‑2‑oxoethylidene)
thiazolidine‑2,4‑dione (3a)
(ppm) 13.34 (brs, 1H, NH), 9.84 (s, 1H, NH) 7.12 (s.1H),
6.89–692 (m,1H), 7.27–7.28 (m, 1 H), 7.29–7.35 (m, 1H),
7.48–7.51(m, 1H), 6.97 (s, 1H, CH=), 3.18 (s, 3H); 13C-
NMR (100 MHz, DMSO-d6): 34.16, 106.72, 111.27, 120.65,
122.66, 126.17, 127.17, 130.83, 131.41, 141.94, 150,61,
155.44, 163.16; MS: (m/z, %), 242 m/z (M+, 27), 215 (43),
198 (44), 143 (75), 170 (36), 130 (48), 111 (43),76 (55),
71.1 (100); Elemental anal. (%), calced for C13H11N3O2: C,
64.72; H, 4.60; N, 17.42; found: C, 63.06; H, 3.25; N, 16.29.
IR (KBr, vmax, cm−1): 3438 (N–H), 1682 (C=O stretching),
3025 (Ar–CH),1542 cm−1; 1H NMR (DMSO-d6): δ=3.56
(s, 3H, OCH3), 6.70 (s, 1H CH=), 7.37–7.38 (d, J=8.8 Hz,
2H, ArH), 8.12–8.13 (d, J=8.8 Hz, 2H, ArH), 12.66 (brs,
1H, NH); 13C NMR (DMSO-d6): ppm 58.10, 103.48, 122.66,
130.83, 131.41, 141.94, 149.36, 170.31, 171.31, 180.04,
182.03; MS: (m/z, %) 263 (M+, 11), 248 (%8),235.9 (9),
220.01 (13), 206.0 (44), 191.0 (9), 177.0 (14), 162.0 (8),
140.1 (16), 134 (100), 121.0 (14), 109 (48), 91.0 (35),
77.0 (35), 51.0 (29), (%) Elemental anal. (%), calced for
C12H9NO4S:C, 54.75; H, 3.45; N, 5.32; found: C, 54.15; H,
2.95; N, 6.12.
2.3.9 (Z)‑5‑((5‑nitrothiophen‑2‑yl)methylene)
thiazolidine‑2,4‑dione (5a)
IR (KBr): νmax 3438 (N–H), 1683 (N–C=O), 3054 (Ar–CH)
cm−1; 1H-NMR (400 MHz, DMSO-d6): δ (ppm), 13.08 (brs,
1H, NH), 8.05–8.06 (dd, 1H), 8.36–8.37 (s.1H, CH=), 7.56
(dd, 1H); 13C-NMR (100 MHz, DMSO-d6): 123.22, 130.09,
140.96, 144.37, 144.38, 145.37, 155.36, 167.32, 168.32;
MS: (m/z, %), 255 m/z (M+, 27), 212 (51), 184 (54), 152
(45), 180 (26), 127 (68), 102 (43), 71.1 (100); Elemental
anal. (%), calced for C8H4N2O4S2: C, 37.50; H, 1.57; N,
10.93; found: C, 36.06; H, 1.05; N, 11.29.
2.3.6 (Z)‑5‑(2‑(4‑methoxyphenyl)‑2‑oxoethylidene)
imidazolidine‑2,4‑dione (3b)
IR (KBr, vmax, cm−1):3433(N–H), 1701 (C=O), 1643 (C=C),
1189 cm−1;1H NMR (DMSO-d6, 400 MHz): δ = 3.83 (s,
3H, OCH3),), 6.95 (s, 1H, CH=), 6.93 (d, J = 8.8 Hz, 2H,
ArH), 7.31 (d, J=8.8 Hz, 2H, ArH), 7.70 (1H, NH); 11.71
(brs, 1H, NH);13C NMR (DMSO-d6): ppm 56.92, 103.26,
125.66, 128.13, 136.68, 144.38, 151.08, 168.44, 187.58,
187.71, 189.8; MS: (m/z, %) 246 (M+, 11), 248 (4), 207
(53), 188.9 (28), 167 (33), 143 (80), 162 (6), 125 (28), 111
(24),85 (55), 71.1 (66), 57.01 (100); Elemental anal. (%),
calced for C12H10NO4: C, 58.54; H, 4.09; N, 11.38; found:
C, 59.06; H, 3.25; N, 10.29.
2.3.10 (Z)‑5‑((5‑nitrothiophen‑2‑yl)methylene)
imidazolidine‑2,4‑dione (5b)
IR (KBr): νmax 3445(N–H), 1722 (N–C=O), 3050 (Ar–CH)
cm−1; 1H-NMR (400 MHz, DMSO-d6): δ (ppm): 12.91 (brs,
1H, NH), 10.68 (s, 1H, NH), 7.14–7.16 (dd, 1H), 7.91–7.92
(dd.1H), 6.97 (s,1H, CH=); 13C-NMR (100 MHz, DMSO-
d6): 114.49, 130.09, 132.87, 140.95, 148.12, 155.36, 162.79,
168.07; MS: (m/z, %), 239 m/z (M+, 46), 195 (54), 168 (46),
136 (35), 127 (68),111(39), 102 (25), 71.1 (100); Elemen-
tal anal. (%), calced for C8H5N3O4S:C, 40.17; H, 2.11; N,
17.57; found: C, 39.06; H, 1.15; N, 16.29.
2.3.7 (Z)‑5‑((1‑methyl‑1H‑indol‑2‑yl)methylene)
thiazolidine‑2,4‑dione (4a)
IR (KBr): νmax 3435 (N–H), 1729, 1685 (N–C=O),
600–800(C-S), 3132 (Ar–CH) cm−1; 1H-NMR (400 MHz,
1 3