Synthesis and spectral data
3-((7-Chloroquinolin-4-yl)amino)-2-(4-fluorophenyl)thiazolidin-4-one (4a)
Yield: 85%, m.p. 282 °C; IR (KBr, cm−1): 3215 (NH), 2924 (CH stretch of CH2), 1668 (C=O), 1612 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.71 (s, 1H, CH-Thiaz), 7.30–7.39 (m, 3H, Ar-H), 7.51 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.84 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.88–7.94 (m, 3H, Ar-H), 8.26–8.40 (m, 3H, Ar-H), 11.42 (s, 1H, NH)
2-(2-Chlorophenyl)-3-((7-chloroquinolin-4-yl)amino)thiazolidin-4-one (4b)
Yield: 61%, m.p. 280 °C; IR (KBr, cm−1): 3230 (NH), 2924 (CH stretch of CH2), 1608 (C=O), 1585 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.75 (s, 1H, CH-Thiaz), 7.28–7.30 (m, 3H, Ar-H), 7.46 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.74 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.81–7.93 (m, 3H, Ar-H), 8.30–8.55 (m, 3H, Ar-H), 11.40 (s, 1H, NH)
4-(4-Chlorophenyl)-3-((7-chloroquinolin-4-yl)amino)thiazolidin-2-one (4c)
Yield: 67%, m.p. 150 °C; IR (KBr, cm−1): 3232 (NH), 2924 (CH stretch of CH2), 1608 (C=O), 1577 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.71 (s, 1H, CH-Thiaz), 7.25–7.33 (m, 3H, Ar-H), 7.49 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.79 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.83–7.89 (m, 3H, Ar-H), 8.22–8.48 (m, 3H, Ar-H), 11.40 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-2-(2,3-dichlorophenyl)thiazolidin-4-one (4d)
Yield: 73%, m.p. 300 °C; IR (KBr, cm−1): 3236 (NH), 2904 (CH stretch of CH2), 1664 (C=O), 1618 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.69 (s, 1H, CH-Thiaz), 7.25–7.33 (m, 3H, Ar-H), 7.45 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.72 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.80–7.87 (m, 3H, Ar-H), 8.30–8.51 (m, 2H, Ar-H), 11.48 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-4-(2,4-dichlorophenyl)thiazolidin-2-one (4e)
Yield: 77%, m.p. > 300 °C; IR (KBr, cm−1): 3240 (NH), 2904 (CH stretch of CH2), 1662 (C=O), 1616 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.71 (s, 1H, CH-Thiaz), 7.49–7.53 (m, 2H, Ar-H), 7.58 (d, 1H, J = 11.2 Hz, CH2-Thiaz), 7.94 (s, 2H, Ar-H), 8.16 (d, 1H, J = 8.4 Hz, CH2-Thiaz), 8.46–8.82 (m, 4H, Ar-H), 12.56 (s, 1H, NH)
2-(4-Bromophenyl)-3-((7-chloroquinolin-4-yl)amino)thiazolidin-4-one (4f)
Yield: 81%, m.p. 140 °C; IR (KBr, cm−1): 3244 (NH), 2908 (CH stretch of CH2), 1662 (C=O), 1618 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.74 (s, 1H, CH-Thiaz), 7.21-7.30 (m, 3H, Ar-H), 7.43 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.72 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.80–7.91 (m, 3H, Ar-H), 8.26–8.51 (m, 2H, Ar-H), 11.52 (s, 1H, NH)
2-(3-Bromo-4-fluorophenyl)-3-((7-chloroquinolin-4-yl)amino)thiazolidin-4-one (4g)
Yield: 66%, m.p. 294 °C; IR (KBr, cm−1): 3238 (NH), 2924 (CH stretch of CH2), 1668 (C=O), 1612 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.71 (s, 1H, CH-Thiaz), 7.28–7.38 (m, 3H, Ar-H), 7.44 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.76 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.88–7.96 (m, 3H, Ar-H), 8.28–8.51 (m, 2H, Ar-H), 11.48 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-4-(4-methoxyphenyl)thiazolidin-2-one (4h)
Yield: 62%, m.p. 260 °C; IR (KBr, cm−1): 3228 (NH), 2895 (CH stretch of CH2), 1670 (C=O), 1612 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.78 (s, 1H, CH-Thiaz), 3.81 (s, 3H, OCH3), 7.01–7.06 (m, 3H, Ar-H), 7.34 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.57 (d, 1H, J = 8.4 Hz, CH2-Thiaz), 7.74–7.84 (m, 3H, Ar-H), 8.37–8.48 (m, 3H, Ar-H), 12.56 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-2-(3,4-dimethoxyphenyl)thiazolidin-4-one (4i)
Yield: 60%, m.p. 130 °C; IR (KBr, cm−1): 3246 (NH), 2893 (CH stretch of CH2), 1610 (C=O), 1550 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.68 (s, 1H, CH-Thiaz), 3.18 (s, 3H, OCH3), 3.34 (s, 3H, OCH3), 7.35–7.44 (m, 2H, Ar-H), 7.56 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.82 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.89–8.05 (m, 3H, Ar-H), 8.33–8.52 (m, 3H, Ar-H), 12.42 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-4-(3,4,5-trimethoxyphenyl)thiazolidin-2-one (4j)
Yield: 50%, m.p. 280 °C; IR (KBr, cm−1): 3226 (NH), 2929 (CH stretch of CH2), 1651 (C=O), 1608 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.72 (s, 1H, CH-Thiaz), 3.71 (s, 3H, OCH3), 3.86 (s, 6H, OCH3), 7.34 (d, 1H, J = 8.0 Hz, CH2-Thiaz), 7.38 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.51–7.98 (m, 4H, Ar-H), 8.33–8.44 (m, 3H, Ar-H), 11.56 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-2-(4-nitrophenyl)thiazolidin-4-one (4k)
Yield: 61%, m.p. > 300 °C; IR (KBr, cm−1): 3334 (NH), 2937 (CH stretch of CH2), 1614 (C=O), 1577 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.75 (s, 1H, CH-Thiaz), 7.37–7.49 (m, 3H, Ar-H), 7.54 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.81 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.90–8.10 (m, 3H, Ar-H), 8.38–8.62 (m, 3H, Ar-H), 11.56 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-4-(4-hydroxyphenyl)thiazolidin-2-one (4l)
Yield: 62%, m.p. > 300 °C; IR (KBr, cm−1): 3192 (NH), 2958 (CH stretch of CH2), 1697 (C=O), 1608 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.72 (s, 1H, CH-Thiaz), 6.82–7.21 (m, 4H, Ar-H), 7.42 (d, 1H, J = 7.6 Hz, CH2-Thiaz), 7.60 (d, 1H, J = 8.0 Hz, CH2-Thiaz), 8.19–8.52 (m, 5H, Ar-H), 9.82 (s, 1H, OH), 11.01 (s, 1H, NH)
4-(3-((7-Chloroquinolin-4-yl)amino)-2-oxothiazolidin-4-yl)benzonitrile (4m)
Yield: 58%, m.p. > 300 °C; IR (KBr, cm−1): 3228 (NH), 2858 (CH stretch of CH2), 1664 (C=O), 1610 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.71 (s, 1H, CH-Thiaz), 7.43 (d, 1H, J = 7.8 Hz, CH2-Thiaz), 7.47–7.95 (m, 4H, Ar-H), 8.10 (d, 1H, J = 8.4 Hz, CH2-Thiaz), 8.53–8.95 (m, 5H, Ar-H), 12.20 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-2-(4-(dimethylamino)phenyl)thiazolidin-4-one(4n)
Yield: 60%, m.p. 195 °C; IR (KBr, cm−1): 3219 (NH), 2899 (CH of CH2), 1664 (C=O), 1608 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.72 (s, 1H, CH-Thiaz), 3.24 (s, 6H, CH3), 6.75–7.33 (d, 4H, J = 8.0 Hz, Ar-H), 7.48 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.61 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.87–8.47 (m, 5H, Ar-H), 11.91 (s, 1H, NH)
3-((7-Chloroquinolin-4-yl)amino)-2-(thiophen-2-yl)thiazolidin-4-one (4o)
Yield: 67%, m.p. > 300 °C; IR (KBr, cm−1): 3192 (NH), 2897 (CH stretch of CH2), 1618 (C=O), 1570 (C=N); 1H-NMR (400 MHz; DMSO-d6): δ = 2.78 (s, 1H, CH-Thiaz), 6.83–7.02 (m, 3H, Ar-H), 7.38 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.65 (d, 1H, J = 8.8 Hz, CH2-Thiaz), 7.70–7.82 (m, 3H, Ar-H), 8.38–8.56 (m, 3H, Ar-H), 11.82 (s, 1H, NH)