3140
R. K. Rawal et al. / Bioorg. Med. Chem. 15 (2007) 3134–3142
+
110.28, 51.77, 33.26, 23.44; ESI-MS: m/z 376 [M+1]
and 398 [M+Na ].
H -pyrimidine), 8.03–8.08 (dd, J = 1.88 and 7.58 Hz,
5
+
+
2H, Ar-H); ESI-MS: m/z 454 [M] , and 476 [M+Na ].
+
4
.4.9. 2-(2,6-Difluorophenyl)-3-(4-phenyl-6-trifluorometh-
4
.4.4. 2-(2,6-Dichlorophenyl)-3-(4-methyl-6-phenylpyrim-
ylpyrimidin-2-yl)thiazolidin-4-one (4i). This compound
was obtained as solid in 32% yield, mp 156–158 °C; IR
idin-2-yl)thiazolidin-4-one (4d). This compound was ob-
tained as solid in 48% yield, mp 168–170 °C; IR
ꢀ
1
1
ꢀ
1
1
(KBr): m
C@O 1726 cm
;
H NMR (200 MHz,
(
KBr): m
C@O 1717 cm
;
H NMR (200 MHz,
max
max
CDCl ) d: 3.93 (d, J = 16.06 Hz, 1H, 5-H ), 4.18 (d,
CDCl ) d: 2.53 (s, 1H, CH ), 3.91 (d, J = 15.75 Hz,
3
A
3
3
J = 16.00 Hz, 1H, 5-H ), 6.86 (t, 2H, H and H -Ph),
1
H ), 7.08 (t, 2H, H and H -Ph), 7.19 (s, 1H, H -pyrim-
H, 5-H ), 4.16 (dd, J = 1.75 and 15.77 Hz, 1H, 5-
B
3
5
A
7
Ar-H), 7.71 (s, 1H, H -pyrimidine), 8.06–8.11 (dd, J =
.01 (s, 1H, H-2), 7.23 (m, 1H, H -Ph), 7.49 (m, 3H,
4
B
3
5
5
idine), 7.22 (m, 1H, H -Ph), 7.28–7.43 (m, 3H, Ar-H),
4
5
1
.96 and 8.06 Hz, 2H, Ar-H); C NMR (75 MHz,
3
1
7
and 7.95 Hz, 2H, Ar-H); ESI-MS: m/z 416 [M+1] and
.49 (d, J = 1.60 Hz, 1H, H-2), 7.85–7.90 (dd, J = 2.23
+
CDCl ) d: 169.00, 168.02, 166.72, 160.87, 157.56,
3
+
1
(
3
55.89, 133.78, 131.06, 128.31, 127.86 (2C), 126.43
2C), 117.11, 111.33, 110.70, 110.37, 106.98, 57.71,
4
5
9
38 [M+Na ]. Anal. Calcd for C H Cl N OS: C,
20 15 2 3
7.70; H, 3.63; N, 10.09. Found: C, 57.46; H, 3.49; N,
.95.
+
4.21; ESI-MS: m/z 437 [M] and 460 [M+Na ].
+
4
2
.4.10. 2-(2,6-Dichlorophenyl)-3-(4,6-diphenylpyrimidin-
- yl)thiazolidin-4-one (4j). This compound was obtained
4
.4.5. 2-(2-Chloro-6-fluorophenyl)-3-(4-methyl-6-phenyl-
pyrimidin-2-yl)thiazolidin-4-one (4e). This compound
as solid in 38% yield, mp 206–208 °C; IR (KBr): m
C@O 1717 cm ; H NMR (200 MHz, CDCl ) d: 3.93
max
was obtained as solid in 41% yield, mp 138–140 °C; IR
ꢀ
1 1
ꢀ
1
1
3
(
KBr): m
C@O 1718 cm
;
H NMR (200 MHz,
max
(
1
d, J = 15.74 Hz, 1H, 5-H ), 4.19 (dd, J = 1.54 and
6.11 Hz, 1H, 5-H ), 7.09–7.50 (m, 11H, Ar-H), 7.84
B
A
CDCl ) d: 2.54 (s, 1H, CH ), 3.84 (d, J = 15.67 Hz,
1
2
pyrimidine), 7.30 (s, 1H, H-2), 7.36–7.43 (m, 3H, Ar-
H), 7.86–7.91 (dd, J = 2.30 and 7.85 Hz, 2H, Ar-H);
ESI-MS: m/z 400 [M+1] and 422 [M+Na ].
3
3
H, 5-H ), 4.17 (d, J = 15.81 Hz, 1H, 5-H ), 6.89 (m,
A B
(s, 1H, H-2), 7.99–8.04 (m, 2H, Ar-H and 1H, H -pyrim-
idine); ESI-MS: m/z 478 [M+1] and 500 [M+Na ].
Anal. Calcd for C H Cl N OS: C, 62.77; H, 3.58; N,
2
5
H, H and H -Ph), 6.92–7.14 (m, 2H, H -Ph and H -
3
5
4
5
+
+
2
5
17
3
+
+
8.78. Found: C, 62.73; H, 3.74; N, 8.55.
4
.4.11. 2-(2-Chloro-6-fluorophenyl)-3-(4,6-diphenylpyrim-
4
.4.6. 2-(2,6-Difluorophenyl)-3-(4-methyl-6-phenylpyrimi-
idin-2-yl)thiazolidin-4-one (4k). This compound was ob-
tained as solid in 30% yield, mp 176–178 °C; IR
din-2-yl)thiazolidin-4-one (4f). This compound was
obtained as solid in 37% yield, mp 165–168 °C; IR
ꢀ1
1
(KBr): m
C@O 1723 cm
;
H NMR (200 MHz,
ꢀ
1
1
max
(
KBr): m
C@O 1717 cm
;
H NMR (200 MHz,
max
CDCl ) d: 3.93 (d, J = 15.74 Hz, 1H, 5-H ), 4.19 (dd,
J = 1.54 and 16.11 Hz, 1H, 5-H ), 7.09 (m, 1H, H -
Ph), 7.15-7.22 (m, 2H, H and H -Ph), 7.44-7.50 (m,
8
and 1H, H -pyrimidine); ESI-MS: m/z 462 [M] and
4
3
A
CDCl ) d: 2.54 (s, 1H, CH ), 3.82 (dd, J = 1.77 and
3
3
B
4
1
6
7
3
7.79 Hz, 1H, 5-H ), 4.21 (d, J = 17.79 Hz, 1H, 5-H ),
.81 (t, 2H, H and H -Ph), 7.06 (s, 1H, H -pyrimidine),
A B
3
5
3
5
5
H, Ar-H), 7.85 (s, 1H, H-2), 8.01–8.06 (m, 2H, Ar-H
.15 (m, 1H, H -Ph), 7.31 (s, 1H, H-2), 7.40–7.46 (m,
4
H, Ar-H), 7.90–7.95 (dd, J = 2.73 and 7.83 Hz, 2H,
+
5
+
84 [M+Na ].
1
3
Ar-H); C NMR (75 MHz, CDCl ) d: 168.96, 168.02,
3
1
1
1
63.34, 160.97, 157.66, 155.89, 134.82, 129.76, 128.09,
27.49 (2C), 125.89 (2C), 117.31, 111.33, 110.70,
10.37, 52.22, 33.42, 23.12; ESI-MS: m/z 384 [M+1]
4
2
.4.12. 2-(2,6-Difluorophenyl)-3-(4,6-diphenylpyrimidin-
-yl)thiazolidin-4-one (4l). This compound was obtained
+
as solid in 28% yield, mp 192–194 °C; IR (KBr): m
C@O 1726 cm ; H NMR (200 MHz, CDCl ) d: 3.86
+
max
and 406 [M+Na ].
ꢀ1
1
3
(dd, J = 1.76 and 15.85 Hz, 1H, 5-H ), 4.24 (d,
J = 15.65 Hz, 1H, 5-H ), 6.83 (t, 2H, H and H -Ph),
A
4.4.7. 2-(2,6-Dichlorophenyl)-3-(4-phenyl-6-trifluorom-
ethylpyrimidin-2-yl)thiazolidin-4-one (4g). This com-
B
3
5
7
7
.12–7.20 (m, 1H, H -Ph), 7.45–7.51 (m, 8H, Ar-H),
4
pound was obtained as solid in 46% yield, mp 206–
2
.86 (s, 1H, H-2), 8.04–8.09 (m, 2H, Ar-H and 1H,
ꢀ
1
1
1
3
08 °C; IR (KBr): m
C@O 1724 cm
;
H NMR
max
H -pyrimidine); C NMR (75 MHz, CDCl ) d: 169.00,
5
3
(200 MHz, CDCl ) d: 3.93 (d, J = 16.06 Hz, 1H, 5-
H ), 4.18 (dd, J = 1.57 and 16.00 Hz, 1H, 5-H ), 7.10–
3
164.59 (2C), 161.07, 157.56, 156.36, 135.26 (2C),
129.85 (2C), 128.16, 127.58 (4C), 126.09 (4C), 117.61,
110.81, 110.51, 107.32, 52.28, 33.44; ESI-MS: m/z 446
A
B
7
.18 (t, 2H, H and H -Ph), 7.31 (m, 1H, H -Ph), 7.46
3 5 4
+
+
(
idine), 8.03–8.08 (dd, J = 1.96 and 8.16 Hz, 2H, Ar-H);
m, 3H, Ar-H), 7.52 (s, 1H, H-2), 7.70 (s, 1H, H -pyrim-
5
[M+1] and 468 [M+Na ].
+
ESI-MS: m/z 470 [M] and 492 [M+Na ].
+
4.4.13. 2-(2,6-Dichlorophenyl)-3-(4,5,6-trimethylpyrimi-
din-2-yl)thiazolidin-4-one (4m). This compound was ob-
4.4.8. 2-(2-Chloro-6-fluorophenyl)-3-(4-phenyl-6-trifluo-
romethylpyrimidin-2-yl)thiazolidin-4-one (4h). This com-
tained as solid in 56% yield, mp 202–204 °C, IR
ꢀ
1
1
(KBr): m
C@O 1718 cm
;
H NMR (300 MHz,
max
pound was obtained as solid in 42% yield, mp 157–
H NMR
CDCl ) d: 2.10 (s, 3H, CH at C -pyrimidine), 2.36
3 3 5
ꢀ
1
1
1
60 °C; IR (KBr): m
C@O 1727 cm
;
(s, 6H, 2CH3 at C4 and C -pyrimidine), 3.90 (dd,
J = 3.42 and 15.66 Hz, 1H, 5-H ), 4.13 (dd, J = 2.04
max
6
(200 MHz, CDCl ) d: 3.93 (d, J = 16.06 Hz, 1H, 5-
H ), 4.19 (d, J = 15.96 Hz, 1H, 5-H ), 6.90 (m, 1H,
3
A
A
B
and 15.66 Hz, 1H, 5-H ), 7.05 (t, 1H, H -Ph), 7.18–
B
4
H -Ph), 7.15–7.18 (m, 2H, H and H -Ph), 7.48 (m,
4
7.21 (dd, J = 1.08 and 7.95 Hz, 1H, H -Ph), 7.25–
3
3
5
3
H, Ar-H), 7.51 (d, J = 1.86 Hz, 1H, H-2), 7.71 (s, 1H,
7.28 (dd, J = 1.35 and 7.74 Hz, 1H, H -Ph), 7.48 (d,
5