Med Chem Res
–NH exchangeable with D2O), 8.03 (1H, s, exocyclic=CH),
6.93–7.48 (8H, m, Ar–H), 3.50 (3H, s, –OCH3), 3.15–3.33
(12H, s, N(CH3)2); 13C NMR (100 MHz, DMSO (d6), d
ppm): 164.92 (C=O), 163.34 (Ar–C, S-triazine ring), 155.
67 (C–OCH3), 139.88 (=CH), 129.62 (C=CH, C5 of thia-
zolidinone), 129.17 (C=N, 4-thiazolidinone), 128.08–119.
44 (Ar–C), 56.90 (–OCH3), 35.73–35.55 (N–(CH3)2); IR
(KBr, cm-1): 3450.67 (–NH str., 2° amine), 1506.28 (ArC–
H str.); TOF–MS (m/z): 492.01 [M?H]?, 134.37.
cm-1): 3434.67 (–NH str., 2° amine), 1347.51 (-NO2), 1551.
27 (–NO2); TOF–MS (m/z): 506.98 [M?H]?, 149.78.
2-[4-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-ylamino)-
phenylimino]-5-(4-trifluoromethyl-benzylidene)-thiaz
olidin-4-one (8o) 1H NMR (400 MHz, DMSO(d6), d
ppm): 8.70 (1H, s, –NH exchangeable with D2O), 8.57 (1H,
s, –NH exchangeable with D2O), 7.90 (1H, s, exocyclic=
CH), 6.89–7.67 (8H, m, Ar–H), 3.10–3.28 (12H, s,
N(CH3)2); 13C NMR (100 MHz, DMSO(d6), d ppm): 165.
08 (C=O), 163.38 (Ar–C, S-triazine ring), 133.76 (=CH),
132.07 (Ar–C–CF3), 128.64 (C=CH, C5 of thiazolidinone),
129.67 (C=N, thiazolidinone), 128.39 (–CF3), 126.81-119.
23 (9C, Ar–C), 35.67–35.59 ((CH3)2); IR (KBr, cm-1):
3425.07 (–NH str., 2° amine), 1508.22 (ArC-H str.), 1288.
06 (C–F str.); TOF–MS (m/z): 530.08 [M?H]?.
2-[4-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-ylamino)-
phenylimino]-5-(3,4-dimethoxy-benzylidene)-thiazoli-
din-4-one (8l) 1H NMR (400 MHz, DMSO(d6), d ppm):
8.85 (1H, s, –NH exchangeable with D2O), 8.70 (1H, s,
–NH exchangeable with D2O), 7.93 (1H, s, exocyclic=CH),
6.91–7.60 (7H, m, Ar–H), 3.51 (6H, s, –OCH3), 3.09–3.23
(12H, s, 2N(CH3)2); 13C NMR (100 MHz, DMSO (d6), d
ppm): 165.13 (C=O), 163.58 (Ar–C, S-triazine ring), 154.
36 (C–OCH3), 153.95 (C–OCH3), 134.10 (=CH), 129.44
(C=CH, C5 of thiazolidinone), 129.30 (C=N, thiazolidi-
none), 128.86–119.19 (Ar–C), 56.82 (–OCH3), 56.85 (–OCH3),
35.68-35.41 (N–(CH3)2); IR (KBr, cm-1): 3419.79 (–NH
str., 2° amine), 1507.54 (ArC–H str.); TOF–MS (m/z): 521.
49 [M?H]?, 165.22.
2-[4-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-ylamino)-
phenylimino]-5-(1H-pyrrol-2-ylmethylene)-thiazolidin-
4-one (9a) 1H NMR (400 MHz, DMSO(d6), d ppm): 8.
69 (1H, s, –NH exchangeable with D2O), 8.36 (1H, s, –NH
exchangeable with D2O), 7.75 (1H, s, exocyclic=CH), 7.
01–7.83 (4H, m, Ar–H), 6.98 (1H, dd, –CH, pyrrole), 6.42
(1H, dd, –CH, pyrrole), 5.92 (1H, t, –CH, pyrrole), 3.08–3.
29 (12H, s, 2N(CH3)2); 13C NMR (100 MHz, DMSO(d6), d
ppm): 165.12 (C=O), 163.61 (Ar–C, S-triazine ring), 133.
98 (=CH), 129.33 (C=CH, C5 of thiazolidinone), 129.26
(C=N, thiazolidinone), 128.78–119.16 (Ar–C), 117.14
(pyrrole), 115.94 (pyrrole), 110.63 (pyrrole), 35.63–35.56
(N–(CH3)2); IR (KBr, cm-1): 3433.86 (–NH str., 2°
amine), 1509.57 (ArC–H str.); TOF–MS (m/z): 435.15
[M?H]?.
2-[4-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-ylamino)-
phenylimino]-5-(4-nitro-benzylidene)-thiazolidin-4-one
(8m) 1H NMR (400 MHz, DMSO(d6), d ppm): 8.87 (1H,
s, Ar–H, adjacent to –NO2 group), 8.70 (1H, s, –NH
exchangeable with D2O), 8.68 (1H, s, –NH exchangeable
with D2O), 8.02 (1H, s, exocyclic=CH), 6.91–7.73 (8H, m,
Ar–H), 3.17–3.25 (12H, s, N(CH3)2); 13C NMR (100 MHz,
DMSO (d6), d ppm): 164.98 (C=O), 163.77 (Ar–C, S-tri-
azine ring), 141.96 (Ar–C–NO2), 134.02 (=CH), 129.38
(C=CH, C5 of thiazolidinone), 129.31 (C=N, thiazolidi-
none), 128.81–119.06 (9C, Ar–C), 35.55–35.49 (N–(CH3)2);
IR (KBr, cm-1): 3428.37 (–NH str., 2° amine); 1341.16
(–NO2), 1548.56 (–NO2); TOF–MS (m/z): 507.58
[M?H]?, 149.99.
2-[4-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-ylamino)-
phenylimino]-5-(1H-indol-2-ylmethylene)-thiazolidin-
4-one (9b) 1H NMR (400 MHz, DMSO(d6), d ppm): 8.
65 (1H, s, –NH exchangeable with D2O), 8.33 (1H, s, –NH
exchangeable with D2O), 7.68 (1H, s, exocyclic=CH), 7.
03–7.88 (8H, m, Ar–H), 6.52 (1H, dd, –CH=CH, indole), 6.
92 (1H, d, –CH=CH–N, indole), 3.06–3.22 (12H, s,
2N(CH3)2); 13C NMR (100 MHz, DMSO(d6), d ppm): 164.
12 (C=O), 163.58 (Ar–C, S-triazine ring), 132.82 (=CH),
129.02 (C=CH, C5 of thiazolidinone), 129.27 (C=N, thia-
zolidinone), 130.64–119.10 (Ar–C), 104.03 (CH=CH–N,
indole), 118.27 (–CH=CH–N, indole), 35.59–35.28 (N–
(CH3)2); IR (KBr, cm-1): 3430.01 (–NH str., 2°
amine),1504.11 (ArC–H str.), 1383.68 (C–N str.); TOF–
MS (m/z): 501.66 [M?H]?.
2-[4-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-ylamino)-
phenylimino]-5-(3-nitro-benzylidene)-thiazolidin-4-one
(8n) 1H NMR (400 MHz, DMSO(d6), d ppm): 8.85 (1H, s,
Ar–H, adjacent to –NO2 group), 8.70 (1H, s, –NH
exchangeable with D2O), 8.72 (1H, s, –NH exchangeable
with D2O), 8.01 (1H, s, exocyclic=CH), 6.91–7.83 (8H, m,
Ar–H), 3.17–3.21 (12H, s, N(CH3)2); 13C NMR (100 MHz,
DMSO(d6), d ppm): 165.03 (C=O), 163.80 (Ar–C, S-triazine
ring), 141.88 (Ar–C–NO2), 133.73 (=CH), 129.45 (C=CH,
C5 of thiazolidinone), 129.58 (C=N, thiazolidinone), 127.
51–119.12 (Ar–C), 35.43–35.59 (N–(CH3)2); IR (KBr,
2-[4-(4,6-Bis-dimethylamino-[1,3,5]triazin-2-ylamino)-
phenylimino]-5-thiophen-3-ylmethylene-thiazolidin-4-
one (9c) 1H NMR (400 MHz, DMSO(d6), d ppm): 8.71
123