Synthesis of substituted thiazolidin-4-one derivatives
1797
OH), 7.91 (d, J = 8.4 Hz, 1H), 7.74 (d, J = 7.6 Hz, CDCl3) δ: 165.8, 164.2, 155.3, 154.9, 139.4, 136.1,
1H), 7.68 (d, J = 8.8 Hz, 1H), 7.63-7.53 (m, 3H), 7.49- 134.6, 133.9, 133.5, 131.4, 131.2, 130.6, 129.9, 129.8,
7.45 (m, 1H), 7.35-7.30 (m, 5H), 7.09 (s, 1H), 7.07 (d, 129.6, 128.8, 128.7, 128.0, 127.9, 127.5, 123.3, 121.1,
J = 8.8 Hz, 1H), 6. 80 (td, J1 = 8.8 Hz, J2 = 2 Hz, 120.0, 118.1, 115.3, 62.7, 62.1, 14.2 ppm; Anal. Calc.
2H), 6.53 (s, 1H), 3.94 (s, 3H, OCH3), 3.74 (s, 3H, for C30H22Cl2N2O4S; C 62.40, H 3.84, N 4.85, S 5.55.
OCH3) ppm; 13C NMR+DEPT (100 MHz, CDCl3) δ: Found: C 62.74, H 3.77, N 4.48, S 5.35%.
166.4 (C), 163.9 (C), 159.1 (C), 154.6 (C), 153.2 (C),
2k: IR (KBr): νmax = 3434, 3068, 2985, 1726, 1699,
139.7 (C), 133.5 (C), 132.8 (C), 131.5 (C), 129.9 (CH),
129.8 (CH), 128.9, 128.8 (CH), 128.7 (CH), 127.8
(CH), 127.0 (CH), 122.9 (CH), 121.4 (CH), 120.3 (CH),
117.5 (CH), 115.9 (C), 114.2 (CH), 65.7 (CH), 55.2
(CH3), 52.9 (CH3) ppm. Anal. Calc. for C30H24N2O5S:
C 68.69, H 4.61, N 5.34, S 6.11%. Found: C 68.36, H
4.99, N 5.70, S 6.27%.
1652 cm−1; 1H NMR (400 MHz, CDCl3) δ: 9.74 (s, 1H,
OH), 7.88 (d, J = 8.4 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H),
7.70 (d, J = 8.8 Hz, 1H), 7.64-7.54 (m, 3H), 7.50-7.46
(m, 1H), 7.35-7.30 (m, 5H), 7.25 (td, J1 = 8.4 Hz, J2 =
2.4 Hz, 2H), 7.10 (s, 1H), 7.07 (d, J = 8.8 Hz, 1H), 6.55
(s, 1H), 4.39 (q, J = 7.2 Hz, 2H, OCH2CH3), 1.41(t,
J = 7.2 Hz, 3H, OCH2CH3) ppm; 13C NMR+DEPT
2h: IR (KBr): νmax = 3374, 3061, 2949, 1731, 1690, (100 MHz, CDCl3) δ: 166.0 (C), 164.0 (C), 154.7 (C),
1644 cm−1; 1H NMR (400 MHz, CDCl3) δ: 10.0 (s, 1H, 154.2 (C), 139.2 (C), 139.1 (C), 133.7 (C), 133.4 (C),
OH), 7.90 (d, J = 8.4 Hz, 1H), 7.74 (d, J = 7.2 Hz, 1H), 131.4 (C), 130.2 (CH), 129.9 (CH), 129.1 (CH), 128.9
7.68 (d, J = 8.8 Hz, 1H), 7.57-7.44 (m, 4H), 7.32-7.29 (CH), 128.8 (CH), 128.7 (C), 127.7 (CH), 127.1 (CH),
(m, 3H), 7.25 (td, J1 = 8.8 Hz, J2 = 2.8 Hz, 2H), 7.09 123.1 (CH), 121.2 (CH), 120.3 (CH), 118.3 (CH), 115.4
(s, 1H), 7.06 (d, J = 8.8 Hz, 1H), 6.69 (td, J1 = 8.8 Hz, (C), 65.3 (CH), 62.2 (CH2), 14.2 (CH3) ppm; Anal.
J2 = 2.8 Hz, 2H), 6.51 (s, 1H), 5.68 (s, 1H, OH), 3.94 Calc. for C30H23ClN2O4S; C 66.35, H 4.27, N 5.16, S
(s, 3H, OCH3) ppm; 13C NMR (100 MHz, CDCl3) δ: 5.90%. Found: C 66.55, H 4.15, N 5.03, S 5.61%.
166.5, 164.0, 155.5, 154.4, 153.3, 139.8, 133.4, 132.6,
2l: IR (KBr): νmax = 3430, 3065, 2983, 1726, 1697,
131.5, 129.9, 128.9, 128.8, 128.7, 127.7, 127.0, 123.0,
121.5, 120.2, 117.6, 115.9, 115.7, 65.7, 53.0 ppm. Anal.
Calc. for C29H22N2O5S: C 68.22, H 4.34, N 5.49, S
6.28%. Found: C 68.11, H 4.18, N 5.47, S 5.56%.
1637 cm−1; 1H NMR (400 MHz, CDCl3) δ: 9.36 (s, 1H,
OH), 7.88 (d, J = 8.4 Hz, 1H), 7.76 (d, J = 8.4 Hz,
1H), 7.73 (d, J = 8.8 Hz, 1H), 7.59-7.46 (m, 4H), 7.42
(dd, J1 = 8.0 Hz, J2 = 0.8 Hz, 1H), 7.34-7.30 (m, 3H),
2i: IR (KBr): νmax = 3456, 3141, 3071, 1726, 1680, 7.25 (dd, J1 = 7.6 Hz, J2 = 1.6 Hz, 1H), 7.18 (dt,
1639 cm−1; 1H NMR (400 MHz, CDCl3) δ: 9.84 (s, 1H, J1 = 8.0 Hz, J2 = 1.6 Hz, 1H), 7.11 (d, J = 8.8 Hz,
OH), 7.94 (d, J = 8.8 Hz, 1H), 7.75 (d, J = 7.2 Hz, 1H), 7.07 (dd, J1 = 7.6 Hz, J2 = 1.2 Hz, 1H), 7.04 (s,
1H), 7.69 (d, J = 9.2 Hz, 1H), 7.63-7.54 (m, 3H), 1H), 6.91 (s, 1H), 4.34 (q, J = 7.2 Hz, 2H, OCH2CH3),
7.50-7.40 (m, 3H), 7.35-7.30 (m, 4H), 7.27-7.21 (m, 1.37 (t, J = 7.2 Hz, 3H, OCH2CH3) ppm; 13C NMR
2H), 7.09 (s, 1H), 7.07 (s, 1H), 6.58 (s, 1H), 4.39 (q, (100 MHz, CDCl3) δ: 165.8, 164.3, 154.9, 154.8, 139.7,
J = 7.2 Hz, 2H, OCH2CH3), 1.41 (t, J = 7.2 Hz, 3H, 137.5, 133.5, 133.2, 131.6, 130.3, 130.2, 129.9, 129.8,
OCH2CH3) ppm; 13C NMR+DEPT (100 MHz, CDCl3) 129.7, 129.4, 128.8, 128.7, 127.9, 127.7, 127.3, 123.2,
δ: 166.0 (C), 164.0 (C), 154.7 (C), 153.8 (C), 140.6 121.4, 120.0, 117.9, 115.7, 63.3, 62.0, 14.2 ppm; Anal.
(C), 139.4 (C), 133.5 (C), 131.6 (C), 130.0 (CH), 129.9 Calc. for C30H23ClN2O4S: C 66.35, H 4.27, N 5.16, S
(CH), 129.8 (CH), 128.9 (CH), 128.8 (CH), 128.7 (C), 5.90%. Found: C 66.88, H 4.27, N 5.03, S 5.75%.
127.9(CH), 127.8 (CH), 127.5 (CH), 127.0 (CH), 122.9
2m: IR (KBr): νmax = 3516, 3078, 2978, 1732, 1697,
(CH), 121.4 (CH), 120.3 (CH), 118.1 (CH), 115.8 (C),
1
1652 cm−1; H NMR (400 MHz, CDCl3) δ: 9.39 (s,
66.1 (CH), 62.2 (CH2), 14.2 (CH3) ppm; Anal. Calc.
for C30H24N2O4S: C 70.85, H 4.76, N 5.51, S 6.30%.
Found: C 70.37, H 4.87, N 5.42, S 6.58%
1H, OH), 8.25 (t, J = 2.0 Hz, 1H), 8.11-8.08 (m, 1H),
7.93 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 7.6 Hz, 1H),
7.74 (d, J = 8.8 Hz, 1H), 7.66-7.51 (m, 5H), 7.41
2j: IR (KBr): νmax = 3437, 3070, 2993, 1727, 1698, (t, J = 8.0 Hz, 1H) 7.38-7.34 (m, 3H), 7.11 (s, 1H),
1651 cm−1; 1H NMR (400 MHz, CDCl3) δ: 9.28 (s, 1H, 7.09 (d, J = 8.8 Hz, 1H), 6.67 (s, 1H), 4.39 (q, J =
OH), 7.82 (d, J = 8.8 Hz, 1H), 7.78-7.73 (m, 2H), 7.2 Hz, 2H, OCH2CH3), 1.40 (t, J = 7.2 Hz, 3H,
7.60-7.44 (m, 5H), 7.35-7.30 (m, 3H), 7.16 (d, J = OCH2CH3) ppm; 13C NMR+DEPT (100 MHz, CDCl3)
8.4 Hz, 1H), 7.11 (d, J = 8.8 Hz, 1H), 7.05 (s, 1H), δ: 165.8 (C), 164.0 (C), 155.3 (C), 154.8 (C), 154.7
7.03 (dd, J1 = 8.8 Hz, J2 = 2.0 Hz, 1H), 6.86 (s, (C), 148.4 (C), 142.8 (C), 138.8 (C), 133.4 (CH), 131.4
1H), 4.34 (q, J = 7.2 Hz, 2H, OCH2CH3), 1.37 (t, J = (C), 130.6 (CH), 130.0 (CH), 129.9 (CH), 129.1 (CH),
7.2 Hz, 3H, OCH2CH3) ppm.; 13C NMR (100 MHz, 128.8 (C), 127.7 (CH), 127.5 (CH), 123.3 (CH), 122.9