Paper
NJC
5-[5-(2-Chloro-phenyl)-furan-2-ylmethylene]-3-(4-methoxy-phenyl)- calculated: C, 67.13; H, 4.22; N, 5.59. S, 6.40; found: C, 67.59; H,
2-(2-methoxy-phenylimino)-thiazolidin-4-one (3e). Light yellow solid; 4.30; N, 5.96; S, 6.59.
yield: 69%; M.p.: 191–192 1C; Rf: 0.56; M.W.: 517.00; FT-IR
1
(nmax; cmÀ1 KBr): 1588 (CQN), 1698 (CQO); H-NMR (300 MHz,
5-[5-(4-Chloro-phenyl)-furan-2-ylmethylene]-2-(4-methoxy-phenyl-
imino)-3-phenyl-thiazolidin-4-one (4a). Light yellow solid; yield:
CDCl3-d6, TMS):d: 3.89 (s, 3H, OCH3), 3.97 (s, 3H, OCH3), 6.82–
7.09 (m 6H, Ar-H), 7.17–7.49 (m, 7H, Ar-H), 7.61 (s, IH, olefinic
59%; M.p.: 118–119 1C; Rf: 0.59; M.W.: 486.97; FT-IR (nmax; cmÀ1
KBr): 1562 (CQN), 1671 (CQO); 1H-NMR (300 MHz, CDCl3-d6,
TMS): d: 3.88 (s, 3H, OCH3), 6.80–7.08 (m, 9H, Ar-H), 7.34–7.42
(m, 4H, Ar-H), 7.56 (s, 1H, olefinic proton), 7.59–7.7.69 (m, 2H,
Ar-H); 13C-NMR (120 MHz, CDCl3): d: 55.64, 114.81, 119.65,
121.17, 124.87, 127.43, 127.88, 128.99, 129.37, 130.34, 131.85,
133.32, 136.05, 138.37, 148.14, 150.05, 151.64, 158.74, 166.79.
Mass: m/z: 487.6 [M + 1]+. Elemental analysis for C27H19ClN2O3S:
calculated: C, 66.59; H, 3.93; N, 5.75; S, 6.58. Found: C, 66.98; H,
3.53; N, 5.65; S, 6.91.
proton), 7.73–7.82 (m, 1H, Ar-H); 13C-NMR (120 MHz, CDCl3):
d: 55.82, 55.94, 108.65, 112.02, 114.26, 114.67, 116.58, 118.22,
119.81, 120.83, 121.08, 122.00, 122.54, 125.51, 125.83, 127.27,
127.85, 129.09, 134.24, 137.72, 149.93, 150.88, 153.27, 155.66,
159.61, 166.49. Mass: m/z: 518.4 [M + 1]+. Elemental analysis for
C28H21ClN2O4S: calculated: C, 65.05; H, 4.09; N, 5.42. S, 6.20.
found: C, 65.88; H, 4.16; N, 5.49; S, 6.30.
5-[5-(2-Chloro-phenyl)-furan-2-ylmethylene]-3-(4-ethoxy-phenyl)-
2-(4-methoxy-phenylimino)-thiazolidin-4-one (3f). Light yellow
solid; yield: 69%; M.p.: 176–177 1C; Rf: 0.56; M.W.: 531.02;
FT-IR (nmax; cmÀ1 KBr): 1589 (CQN), 1681(CQO); 1H-NMR
5-[5-(4-Chloro-phenyl)-furan-2-ylmethylene]-3-(4-fluoro-phenyl)-
2-(4-methoxy-phenylimino)-thiazolidin-4-one (4b). Dark yellow
solid; yield: 65%; M.p.: 137–138 1C; Rf: 0.58; M.W.: 504.96;
FT-IR (nmax; cmÀ1 KBr): 1568 (CQN), 1678 (CQO); 1H-NMR
(400 MHz, CDCl3-d6, TMS): d: 3.86 (s, 3H, OCH3), 6.77–6.80
(m, 2H, Ar-H), 6.92–7.10 (m, 5H, Ar-H), 7.20–7.25 (m, 1H, Ar-H),
7.32–7.39 (m, 2H, Ar-H), 7.43 (s, 1H, olefinic proton), 7.44–7.59
(m, 4H, Ar-H);13C-NMR (120 MHz, CDCl3):d: 55.51 108.39,
114.73, 114.72, 115.75, 115.97, 116.24, 116.47, 116.98, 117.12,
118.58, 118.92, 119.11, 122.45, 122.76, 122.84, 125.51, 125.58,
127.51, 127.76, 127.81, 129.13, 129.17, 129.19, 129.90, 129.99,
134.43, 141.38, 144.57, 144.60, 149.78, 149.82, 151.76, 153.07,
155.90, 155.96, 157.17, 159.76, 166.16, 166.33. Mass: m/z: 504.6
[M+]+. Elemental analysis for C27H18ClFN2O3S: calculated: C,
64.22; H, 3.59; N, 5.55; S, 6.35. Found: C, 64.78; H, 3.68; N,
5.89; S, 6.93.
(400 MHz, CDCl3-d6, TMS): d: 1.43 (t, 3H, OCH2CH3, J =
À À
6.6 Hz), 3.84 (s, 3H, OCH3), 4.05 (q, 2H, OCH2CH3, J =
ÀÀ À
7.1 Hz), 6.82–7.05 (m, 7H, Ar-H), 7.22–7.45 (m, 6H, Ar-H), 7.59
(s, 1H, olefinic proton), 7.78 (s, 1H, Ar-H); 13C-NMR (120 MHz,
CDCl3): d: 14.96, 55.52, 63.71, 114.07, 114.29, 114.67, 114.90,
115.13, 116.61, 118.12, 120.02, 122.52, 127.89, 128.12, 129.10,
129.15, 130.60, 141.70, 149.48, 153.19, 156.37, 156.99, 159.10,
159.66, 166.44. Mass: m/z: 531.12 [M+]+. Elemental analysis for
C
29H23ClN2O4S: calculated: C, 65.59; H, 4.37; N, 5.28; S, 6.04.
Found: C, 65.91; H, 4.43; N, 5.58; S, 6.49.
5-[5-(2-Chloro-phenyl)-furan-2-ylmethylene]-3-(2-methoxy-phenyl)-
2-(4-methoxy-phenylimino)-thiazolidin-4-one (3g). Light brown solid;
yield: 61%; M.p.: 179–180 1C; Rf: 0.57; M.W.: 517; FT-IR
1
(nmax; cmÀ1 KBr); 1595 (CQN), 1688(CQO); H-NMR (400 MHz,
3-(4-Chloro-phenyl)-5-[5-(4-chloro-phenyl)-furan-2-ylmethylene]-
2-(4-methoxy-phenylimino)-thiazolidin-4-one (4c). Light yellow
solid; yield: 62%; M.p.: 165–166 1C; Rf: 0.57; M.W.: 521.41
FT-IR (nmax; cmÀ1 KBr): 1592 (CQN), 1693 (CQO); 1H-NMR
(300 MHz, CDCl3-d6, TMS): d: 3.87 (s, 3H, OCH3), 6.80 (s, 2H,
Ar-H), 6.93–7.09 (m, 5H, Ar-H), 7.31–7.44 (m, 5H, Ar-H), 7.51
(s, 1H, olefinic proton), 7.54–7.59 (m, 2H, Ar-H); 13C-NMR
(120 MHz, CDCl3): d: 55.15, 108.74, 114.34, 114.74, 115.75,
115.95, 116.76, 116.86, 116.96, 118.58, 118.68, 118.98, 119.15,
122.42, 122.77, 122.87, 125.55, 127.17, 127.77, 127.87, 129.15,
129.16, 129.19, 129.97, 134.44, 141.38, 144.54, 144.64, 147.79,
147.89, 151.17, 153.83, 155.93, 157.17, 159.79, 166.16. 166.39.
Mass: m/z: 521.4 [M+]+. Elemental analysis for C27H18Cl2N2O3S:
calculated: C, 62.19; H, 3.48; N, 5.37; S, 6.15. Found: C, 62.69; H,
3.89; N, 5.77; S, 6.69.
CDCl3-d6, TMS): d: 3.83 (s, 6H, 2OCH3), 6.79(d 1H, Ar-H, J =
3.72 Hz), 6.90 (d, 2H, Ar-H, J = 8.88 Hz), 6.92 (d, 2H, Ar-H, J =
6.92 Hz), 7.04 (d, 2H, Ar-H, J = 8.88), 7.19–7.24 (m, 2H, Ar-H), 7.28
(d, 1H, Ar-H, J = 3.72), 7.37–7.43 (m, 3H, Ar-H), 7.56 (s, 1H, olefinic
proton), 7.74–7.76 (m, 1H, Ar-H); 13C-NMR (120 MHz, CDCl3): d:
55.51, 55.52, 114.09, 114.31, 114.67, 116.61, 118.16, 119.99,
122.54, 127.02, 128.09, 129.07, 129.17, 130.58, 130.97, 141.77,
149.96, 152.36, 153.17, 157.02, 159.67, 166.39. Mass: m/z: 517.21
[M+]+. Elemental analysis for C28H21ClN2O4S: calculated: C, 65.05;
H, 4.09; N, 5.42; S, 6.20. Found: C, 65.42; H, 4.69; N, 5.82; S, 6.85.
5-[5-(2-Chloro-phenyl)-furan-2-ylmethylene]-2-(4-methoxy-phenyl-
imino)-3-o-tolyl-thiazolidin-4-one (3h). Light yellow solid; yield:
55%; M.p.: 164–165 1C; Rf: 0.58; M.W.: 501.00; FT-IR (nmax; cmÀ1
KBr): 1570 (CQN), 1675 (CQO); 1H-NMR (300 MHz, CDCl3-d6,
TMS): d: 2.19 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 6.79(s 2H, Ar-H),
6.91–7.07 (m, 6H, Ar-H), 7.32–7.41 (m, 4H, Ar-H), 7.54 (s, 1H,
3-(4-Bromo-phenyl)-5-[5-(4-chloro-phenyl)-furan-2-ylmethylene]-
olefinic proton), 7.57–7.58 (m, 2H, Ar-H); 13C-NMR (120 MHz, 2-(4-methoxy-phenylimino)-thiazolidin-4-one (4d). Light yellow
CDCl3): d: 17.94, 55.53, 114.08, 114.10, 114.31, 114.68, 114.72, solid; yield: 69%; M.p.: 166–167 1C; Rf: 0.57; M.W.: 565.86;
116.60, 116.73, 118.17, 118.22, 120.00, 120.03, 120.17, 122.56, FT-IR (nmax; cmÀ1 KBr): 1599 (CQN), 1673 (CQO); 1H-NMR
124.90, 126.38, 127.03, 128.04, 129.07, 129.13, 129.18, 130.12, (300 MHz, CDCl3-d6, TMS): d: 3.87 (s, 3H, OCH3), 6.81–7.09
130.52, 130.70, 130.93, 13097, 141.78, 147.28, 149.36, 149.45, (m, 6H, Ar-H), 7.35–7.60 (m, 7H, Ar-H), 7.61 (s, 1H, olefinic
151.98, 152.37, 153.16, 153.20, 157.03, 159.67, 159.74, 166.39. proton), 7.67–7.71 (m, 1H, Ar-H); 13C-NMR (120 MHz, CDCl3): d:
Mass: m/z: 502.8 [M + 1]+. Elemental analysis for C28H21ClN2O3S: 55.73, 108.86, 114.06, 115.11, 116.08, 116.70, 118.30, 118.72,
New J. Chem.
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