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& C5) 120.16, 114.49 (pyridin-2-yl-C5 & C3), 62.43 (C2), 35.81 (C5),
24.53, 23.72 (CH3 at C6,4-pyridin-2-yl); MS (ESI): m/z 523 (M+H)+.
Anal. calcd for C15H12Br3N3OS: C, 34.51; H, 2.32; N, 8.05. Found:
C, 34.57; H, 2.38; N, 8.10.
z 429 (M+). Anal. calcd for C14H11Br2N3OS: C, 39.18; H, 2.58; N,
9.79. Found: C, 39.11; H, 2.60; N, 9.82.
4.2.14. 2-(3,5-Dichloro-pyridin-4-yl)-3-(6-methyl-pyridin-2-yl)-
thiazolidin-4-one (14)
4.2.10. 3-(5-Bromo-4,6-dimethylpyridin-2-yl)-2-(3,5-
dichloropyridin-4-yl)thiazolidin-4-one (10)
Light yellow solid, yield: 77.4%. mp: 108–110 °C; IR (KBr): mmax
C@O 1699 cmꢀ1; 1H NMR (300 MHz, CDCl3); d 8.47, 8.32 (s, 2H, H2,
H6-pyridin-4-yl), 8.11 (d, 1H, J = 8.3 Hz, H3-pyridin-2-yl), 7.61 (d,
1H, J = 7.7 Hz, H4-pyridin-2-yl), 7.44 (d, 1H, J = 1.9 Hz, H5-pyridin-
2-yl), 6.88 (s, 1H, CH), 4.21 (dd, 1H, J = 12.8 Hz, 2.2 Hz, CH2), 3.99
(d, 1H, J = 12.9 Hz, CH2), 2.25 (s, 3H, CH3 at C6-pyridin-2-yl); 13C
NMR (75 MHz, CDCl3): d 170.93 (C@O), 156.37 (pyridin-2-yl-C6),
149.66 (pyridin-2-yl-C2), 148.52 (pyridin-4-yl-C2 & C6), 147.71
(pyridin-4-yl-C4), 138.27 (pyridin-2-yl-C4), 131.90, 129.70 (pyri-
din-4-yl-C3 & C5), 120.16 (pyridin-2-yl-C5), 111.92 (pyridin-2-yl-
C3), 58.42 (C2), 35.70 (C5), 23.43 (CH3 at C6-pyridin-2-yl); MS
(ESI): m/z 340.1 (M+). HRMS (ESI): (M+H+), calcd for
White solid, yield: 82.5%. mp: 115–117 °C; IR (KBr): mmax C@O
1691 cmꢀ1 1H NMR (300 MHz, CDCl3); d 8.48, 8.33 (s, 2H, H2,
;
H6-pyridin-4-yl), 8.05 (s, 1H, H3-pyridin-2-yl), 7.39 (s, 1H, CH),
4.20 (dd, 1H, J = 15.9 Hz, 2.03 Hz, CH2), 3.98 (d, 1H, J = 15.9 Hz,
CH2), 2.42 (s, 3H, CH3 at C6-pyridin-2-yl), 2.38 (s, 3H, CH3 at C4-
pyridin-2-yl); 13C NMR (75 MHz, CDCl3): d 171.17 (C@O), 158.09,
152.96 (pyridin-2-yl-C6 & C4), 147.78, 146.34 (pyridin-4-yl-C4,
C2 & C6), 144.79 (pyridin-2-yl-C2), 133.09 (pyridin-4-yl-C3 & C5)
118.16, 116.49 (pyridin-2-yl-C5 & C3), 61.24 (C2), 34.62 (C5),
24.65, 23.45 (CH3 at C6,4-pyridin-2-yl); MS (ESI): m/z 434 (M+H)+.
Anal. calcd for C15H12BrCl2N3OS: C, 41.59; H, 2.79; N, 9.70. Found:
C, 41.61; H, 2.76; N, 9.65.
C
14H11Cl2N3OS+ m/z 339.0000, found 339.0052
4.2.15. 3-(5-Bromo-6-methyl-pyridin-2-yl)-2-(3,5-dibromo-
pyridin-4-yl)-thiazolidin-4-one (15)
4.2.11. 2-(3,5-Dibromopyridin-4-yl)-3-(4,6-dimethylpyridin-2-
yl)thiazolidin-4-one (11)
Light yellow solid, yield: 75.5%. mp: 118–120 °C; IR (KBr): mmax
C@O 1695 cmꢀ1; 1H NMR (300 MHz, CDCl3); d 8.66, 8.49 (s, 2H, H2,
H6-pyridin-4-yl), 8.07 (d, 1H, J = 8.7 Hz, H3-pyridin-2-yl), 7.81 (d,
1H, J = 8.7 Hz, H4-pyridin-2-yl), 7.39 (s, 1H, CH), 4.21 (dd, 1H,
J = 15.9 Hz, 1.9 Hz, CH2), 4.00 (d, 1H, J = 15.9 Hz, CH2), 2.37 (s, 3H,
CH3 at C6-pyridin-2-yl); 13C NMR (75 MHz, CDCl3): d 171.16
(C@O), 155.09 (pyridin-2-yl-C6), 153.01(pyridin-4-yl-C4), 150.87
(pyridin-2-yl-C2), 148.30, 145.63 (pyridin-4-yl-C2 & C6), 141.63
(pyridin-2-yl-C4), 123.22 (pyridin-4-yl-C3 & C5), 116.97 (pyridin-
2-yl-C5), 113.88 (pyridin-2-yl-C3), 62.40 (C2), 35.73 (C5), 23.86
(CH3 at C6-pyridin-2-yl); MS (ESI): m/z 509.8 (M+H+). Anal. calcd
for C14H10Br3N3OS: C, 33.10; H, 1.98; N, 8.27. Found: C, 33.19; H,
1.91; N, 8.36.
Light yellow solid, yield: 80.4%. mp: 114–116 °C; IR (KBr): mmax
C@O 1691 cmꢀ1; 1H NMR (300 MHz, CDCl3); d 8.62, 8.47 (s, 2H, H2,
H6-pyridin-4-yl), 7.88 (s, 1H, H3-pyridin-2-yl), 7.46 (s, 1H, H5-pyri-
din-2-yl), 6.70 (s, 1H, CH), 4.20 (dd, 1H, J = 15.7 Hz, 2.01 Hz, CH2),
4.00 (d, 1H, J = 15.7 Hz, CH2), 2.32 (s, 3H, CH3 at C6-pyridin-2-yl),
2.22 (s, 3H, CH3 at C4-pyridin-2-yl); 13C NMR (75 MHz, CDCl3): d
171.03 (C@O), 155.88 (pyridin-2-yl-C6), 152.84 (pyridin-4-yl-C4),
150.73 (pyridin-2-yl-C4), 149.64 (pyridin-4-yl-C2 & C6), 146.08
(pyridin-2-yl-C2), 123.34 (pyridin-4-yl-C3 & C5), 121.53 (pyridin-
2-yl-C5), 112.94 (pyridin-2-yl-C3), 62.67 (C2), 35.94 (C5), 23.26,
21.31 (CH3 at C6,4-pyridin-2-yl); MS (ESI): m/z 444 (M+H+). Anal.
calcd for C15H13Br2N3OS: C, 40.65; H, 2.96; N, 9.48. Found: C,
40.56; H, 2.90; N, 9.52.
4.2.16. 3-(5-Bromo-6-methyl-pyridin-2-yl)-2-(3,5-dichloro-
pyridin-4-yl)-thiazolidin-4-one (16)
4.2.12. 2-(3,5-Dichloropyridin-4-yl)-3-(4,6-dimethylpyridin-2-
yl)thiazolidin-4-one (12)
Light yellow solid, yield: 77.8%. mp: 120–122 °C; IR (KBr): mmax
C@O 1695 cmꢀ1; 1H NMR (300 MHz, CDCl3); d 8.50, 8.34 (s, 2H, H2,
H6-pyridin-4-yl), 8.09 (d, 1H, J = 8.7 Hz, H3-pyridin-2-yl), 7.80 (d,
1H, J = 8.7 Hz, H4-pyridin-2-yl), 7.37 (s, 1H, CH), 4.26 (dd, 1H,
J = 15.9 Hz, 1.9 Hz, CH2), 3.98 (d, 1H, J = 15.9 Hz, CH2), 2.36 (s, 3H,
CH3 at C6-pyridin-2-yl); 13C NMR (75 MHz, CDCl3): d 170.97
(C@O), 155.08 (pyridin-2-yl-C6), 149.68 (pyridin-2-yl-C2), 148.40
(pyridin-4-yl-C2 & C6), 147.77 (pyridin-4-yl-C4), 141.68 (pyridin-
2-yl-C4), 131.74 (pyridin-4-yl-C3 & C5), 116.86 (pyridin-2-yl-C5),
113.58 (pyridin-2-yl-C3), 58.24 (C2), 35.55 (C5), 23.82 (CH3 at
C6-pyridin-2-yl); MS (ESI): m/z 419.9 (M+). Anal. calcd for
White solid, yield: 81.2%. mp: 117–119 °C; IR (KBr): mmax C@O
1695 cmꢀ1 1H NMR (300 MHz, CDCl3); d 8.47, 8.32 (s, 2H, H2,
;
H6-pyridin-4-yl), 7.90 (s, 1H, H5-pyridin-2-yl), 7.45 (s, 1H, H3- pyri-
din-2-yl), 6.71 (s, 1H, CH), 4.21 (dd, 1H, J = 15.7 Hz, 2.04 Hz, CH2),
3.99 (d, 1H, J = 15.7 Hz, CH2), 2.32 (s, 3H, CH3 at C6-pyridin-2-yl),
2.21 (s, 3H, CH3 at C4-pyridin-2-yl); 13C NMR (75 MHz, CDCl3): d
170.88 (C@O), 155.90 (pyridin-2-yl-C6),150.18 (pyridin-2-yl-C4)
149.72, 149.56 (pyridin-4-yl-C2 & C6), 147.67 (pyridin-4-yl-C4),
144.19 (pyridin-2-yl-C2), 131.96, 129.79 (pyridin-4-yl-C3 & C5),
121.49 (pyridin-2-yl-C5), 112.64 (pyridin-2-yl-C3), 58.50 (C2),
35.81 (C5), 23.27, 21.33 (CH3 at C6,4-pyridin-2-yl); MS (ESI): m/z
354.2 (M+). HRMS (ESI): (M+H+), calcd for C15H13Cl2N3OS+H+ m/z
354.0235, found 354.0193.
C14H10BrCl2N3OS: C, 40.12; H, 2.40; N, 10.03. Found: C, 40.21; H,
2.45; N, 10.16.
4.2.17. 3-(6-Chloro-2-(methylthio)pyrimidin-4-yl)-2-(2-chloro-
6-fluorophenyl)thiazolidin-4-one (17)
4.2.13. 2-(3,5-Dibromo-pyridin-4-yl)-3-(6-methyl-pyridin-2-yl)-
thiazolidin-4-one (13)
White crystals, yield: 78.8%. mp: 120–122 °C; IR (KBr): mmax
Light yellow solid, yield: 78.6%. mp: 110–112 °C; IR (KBr): mmax
C@O 1688 cmꢀ1; 1H NMR (300 MHz, CDCl3); d 8.63, 8.47 (s, 2H, H2,
H6-pyridin-4-yl), 8.09 (d, 1H, J = 8.3 Hz, H3-pyridin-2-yl), 7.62 (d,
1H, J = 7.7 Hz, H4-pyridin-2-yl), 7.46 (d, 1H, J = 2.01 Hz, H5-pyridin-
2-yl), 6.88 (s, 1H, CH), 4.21 (dd, 1H, J = 15.7 Hz, 2.1 Hz, CH2), 4.00
(d, 1H, J = 15.8 Hz, CH2), 2.26 (s, 3H, CH3 at C6-pyridin-2-yl); 13C
NMR (75 MHz, CDCl3): d 171.11 (C@O), 156.37 (pyridin-2-yl-C6),
152.93 (pyridin-4-yl-C4), 150.82 (pyridin-2-yl-C2), 149.58, 145.92
(pyridin-4-yl-C2 & C6), 138.22 (pyridin-2-yl-C4), 123.31 (pyridin-
4-yl-C3 & C5), 118.64 (pyridin-2-yl-C5), 112.24 (pyridin-2-yl-C3),
62.57 (C2), 35.87 (C5), 23.47 (CH3 at C6-pyridin-2-yl); MS (ESI): m/
C@O 1695 cmꢀ1 1H NMR (300 MHz, CDCl3); d 8.12 (s, 1H, H5-pyr-
;
imidin-4-yl), 7.09–7.45 (m, 3H, H3, H4, & H5-PhH), 6.95 (s, 1H, CH),
4.18 (d, 1H, J = 16.14 Hz, CH2), 3.88 (d, 1H, J = 16.13 Hz, CH2), 2.27
(s, 3H, SCH3 at C2- pyrimidin-4-yl); 13C NMR (75 MHz, CDCl3): d
171.36 (C@O), 170.35 (pyrimidin-4-yl-C2), 163.23, 161.83 (pyrim-
idin-4-yl-C6 & C4), 161.83, 135.23, 129.62, 125.97, 125.54, 115.52
(Ph-C), 105.98 (pyrimidin-4-yl-C5), 57.65 (C2), 34.32 (C5), 13.78
(SCH3 at C2- pyrimidin-4-yl); MS (ESI): m/z 390 (M+). HRMS
(ESI): (M+H+), calcd for C14H10Cl2FN3OS2+H+ m/z 389.9626, found
389.9677.