Molecules 2018, 23, 1897
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(Z)-5-(pyridin-4-ylmethylene)-2-thioxothiazolidin-4-one (2i). Yield 30%; Rf = 0.96; Mp = 299 C (294 C [38];
1H-NMR (300 MHz, ppm, DMSO-d6): 7.52–7.54 (m, 2H, pyr.), 7.58 (s, 1H, =CH), 8.72–8.74 (m, 2H, pyr.);
MS: m/z: 220.90 (M−) (222.29). (Supplementary material 2).
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(Z)-5-(2,5-dimethoxybenzylidene)-2-thioxothiazolidin-4-one (2j). Yield 75%; Rf = 0.79; Mp = 240 C;
1H-NMR (300 MHz, ppm, DMSO-d6): 3.76 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 6.87 (s, 1H, arom.),
7.08 (d, J = 1.5 Hz, 2H, arom.), 7.73 (s, 1H, =CH), 13.76 (s, 1H, NH); 13C-NMR (DMSO-d6)
δ (ppm):
195.83, 169.34, 153.19, 152.55, 126.65, 125.70, 121.78, 118.50, 113.87, 113.18, 55.56; MS: m/z: 280.20 (M )
−
(281.35). (Supplementary material 2).
(Z)-5-(4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (2k). Yield 36%; Rf = 0.62; Mp = 285 ◦C; 1H-NMR
(300 MHz, ppm, DMSO-d6): 6.91–6.93 (d, J = 8.8 Hz, 2H, arom.), 7.44–7.46 (d, J = 8.8 Hz, 2H, arom.),
7.55 (s, 1H, =CH), 10.4 (s, 1H, OH), 13.68 (s, 1H, NH); 13C-NMR (DMSO-d6)
δ (ppm): 195.50, 169.48,
160.33, 132.28, 123.93, 120.96, 116.50, MS: m/z: 236.00 (M−) (237.30). (Supplementary material 2).
(Z)-3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxothiazolidin-4-one (2l). Yield 72%;
Rf = 0.58; Mp = 225–227 ◦C; 1H-NMR (300 MHz, ppm, DMSO-d6): 3.85 (s, 3H, OCH3), 6.96–6.99 (d,
J = 8.1 Hz, 1H, arom.), 7.16–7.18 (d, J = 8.1 Hz, 1H, arom), 7.26 (s, 1H, arom.), 7.46–7.47 (d, J = 8.8 Hz
2H, arom.), 7.63–7.64 (d, J = 8.1 Hz, 2H, arom.), 7.76 (s, 1H, =CH), 10.19 (s, 1H, OH); ); 13C-NMR
(DMSO-d6) (ppm): 193.63, 166.85, 150.22, 148.13, 132.10, 130.78, 129.37, 125.12, 124.46, 118.65, 116.44,
,
δ
114.65, 55.65 MS: m/z: 376.20 (M−) (377.85). (Supplementary material 2).
(Z)-3-(4-chlorophenyl)-5-(4-(dimethylamino)benzylidene)-2-thioxothiazolidin-4-one (2m). Yield 48%; Rf = 0.77;
Mp = 249–251 ◦C; 1H-NMR (300 MHz, ppm, DMSO-d6): 3.08 (s, 6H, 2CH3), 6.86–6.88 (m, 2H, arom.),
7.44–7.47 (m, 2H, arom.), 7.52–7.55 (m, 2H, arom), 7.62–7.65 (m, 2H, arom.), 7.73 (s, 1H, =CH); MS: m/z:
375.30 (M+) (374.90). (Supplementary material 2).
(Z)-3-(4-chlorophenyl)-5-(4-hydroxybenzylidene)-2-thioxothiazolidin-4-one (2n). Yield 10%; Rf = 0.72;
Mp = 292–294 ◦C; 1H-NMR (300 MHz, ppm, DMSO-d6): 6.96-6.97 (d, J = 8.8 Hz, 2H, arom.),
7.45–7.47 (m, 2H, arom), 7.55–7.56 (d, J = 8.8 Hz, 2H, arom.), 7.62–7.63 (m, 2H, arom.), 7.76 (s, 1H, =CH),
10.48 (s, 1H, OH); 13C-NMR (DMSO-d6)
δ (ppm): 193.68, 166.86, 160.62, 134.16, 133.63, 133.27, 130.75,
129.25, 124.05, 118.50, 116.64; MS: m/z: 345.90 (M−) (346.85). (Supplementary material 2).
(Z)-3-(4-chlorophenyl)-5-(2,5-dimethoxybenzylidene)-2-thioxothiazolidin-4-one (2o). Yield 32%; Rf = 0.78;
Mp = 170–172 ◦C; 1H-NMR (300 MHz, ppm, DMSO-d6): 3.78 (s, 3H, OCH3), 3.87 (s, 3H, OCH3), 6.99 (s,
1H, arom.), 7.13 (d, J = 1.5 Hz, 2H, arom.), 7.43–7.46 (m, 2H, arom.), 7.60–7.63 (m, 2H, arom.), 7.90 (s,
1H, =CH); 13C-NMR (DMSO-d6)
δ (ppm): 194.70, 167.18, 153.10, 134.57, 131.16, 129.85, 128.81, 122.49,
119.37, 114.95, 113.95, 56.69, 56.22; MS: m/z: 392.00 (M+) (391.89). (Supplementary material 2).
(Z)-2-(5-((1,3-di-p-tolyl-1H-pyrazol-4-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (3a). Yield 75%;
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1
Rf = 0.61; Mp = 240 C (carb.); H-NMR (300 MHz, ppm, DMSO-d6): 2.38 (s, 3H, CH3), 2.41 (s,
3H, CH3), 4.47 (s, 2H, CH2), 7.36–7.40 (m, 4H, arom.), 7.53–7.54 (d, J = 2.3 Hz, 2H, arom.), 7.56 (s,
1H, =CH-.), 7.93–7.96 (d, J = 8.7 Hz, 2H, arom.), 8.78 (s, 1H, pyr); ); 13C-NMR (DMSO-d6)
δ
(ppm):
139.24, 137.59, 136.98, 130.61, 130.20, 129.17, 119.92, 119.72, 116.02, 21.1; MS: m/z: 448.20 (M
(Supplementary material 2).
−
) (449.54).
(Z)-2-(5-((3-(4-fluorophenyl)-1-(p-tolyl)-1H-pyrazol-4-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid
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3b). Yield 72%; Rf = 0.66; Mp = >300 C; 1H-NMR (300 MHz, ppm, DMSO-d6): 2.44 (s, 3H, CH3),
(
4.45 (s, 2H, CH2), 7.36–7.39 (m, 4H, arom.), 7.45 (s, 1H, =CH-), 7.69–7.71 (m, 2H, arom.), 7.93–7.96 (m,
2H, arom.), 8.78 (s, 1H, pyr); ); MS: m/z: 452.10 (M−) (453.51). (Supplementary material 2).
(Z)-2-(5-((3-(4-methoxyphenyl)-1-(p-tolyl)-1H-pyrazol-4-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic
acid (3c). Yield 66%; Rf = 0.70; Mp = 250 ◦C (carb.); 1H-NMR (300 MHz, ppm, DMSO-d6): 2.38 (s, 3H,
CH3), 3.86 (s, 3H, OCH3), 4.59 (s, 2H, CH2), 7.11–7.14 (m, 2H, arom.), 7.35–7.37 (d, J = 8.3 Hz, 2H,
arom.), 7.57 (s, 1H, =CH-), 7.60-7.64 (m, 2H, arom.), 7.90–7.93 (d, J = 8.7 Hz, 2H, arom.), 8.70 (s, 1H,