168
V. Padmavathi et al.
Arch. Pharm. Chem. Life Sci. 2011, 11, 165–169
5-(Bis((5-phenyl-1,3,4-oxadiazol-2-yl)methylthio)-
methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 5a
5-(Bis((5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-
methylthio)methylene)-dihydro-2-thioxopyrimidine-4,6-
Pale yellow solid in 76% yield; m.p.: 145–1478C; IR (KBr) nmax
(1H,5H)-dione 6c
White solid in 69% yield; m.p.: 165–1678C; IR (KBr) nmax [cmꢁ1]:
1
[cmꢁ1]: 3234 (NH), 1656 (CONH), 1637 (C N), 1624 (C C); H-NMR
–
–
–
–
1
3239 (NH), 1650 (CONH), 1633 (C N), 1619 (C C),1491 (C S); H-
(DMSO-d6) d [ppm]: 4.71 (s, 4H, S–CH2), 7.30–7.52 (m, 10H, Ar-H),
–
–
–
–
–
–
11.25 (bs, 2H, NH); 13C-NMR (DMSO-d6) d [ppm]: 38.9 (S-CH2), 105.2
NMR (DMSO-d6) d [ppm]: 4.73 (s, 4H, S-CH2), 7.30–7.45 (m, 8H, Ar-
H), 11.57 (bs, 2H, NH); 13C-NMR (DMSO-d6) d [ppm]: 39.7 (S-CH2),
–
(C C(S)S), 126.3, 127.3, 128.4, 129.6 (aromatic carbons), 151.2
–
–
(HNCO), 160.2 & 164.8 (C2 & C ), 163.7 (C CS(S)), 165.9 (COC C).
–
–
–
–
5
104.2 (C C(S)S), 124.6, 128.0, 129.6, 134.1 (aromatic carbons),
–
–
160.2 & 165.0 (C2 & C ), 163.8 (C CS(S)), 166.4 (COC C), 173.6
Anal. calcd. for C23H16N6O5S2: C, 53.07; H, 3.10; N, 16.14. Found:
C, 53.18; H, 3.15; N, 16.22.
–
–
–
5
–
(C S). Anal. calcd. for C23H14Cl2N6O4S3: C, 45.62; H, 2.33; N, 13.88.
–
Found: C, 45.55; H, 2.38; N, 13.98.
5-(Bis((5-p-tolyl-1,3,4-oxadiazol-2-yl)-
methylthio)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione
5-(Bis((5-phenyl-1,3,4-thiadiazol-2-yl)-
methylthio)methylene)pyrimidine-2,4,6-(1H,3H,5H)-trione
5b
Yellow solid in 64% yield; m.p.: 132–1348C; IR (KBr) nmax [cmꢁ1]:
7a
White solid in 77% yield; m.p.: 162–1648C; IR (KBr) nmax [cmꢁ1]:
1
3226 (NH), 1663 (CONH), 1635 (C N), 1623 (C C); H-NMR (DMSO-
–
–
–
–
1
3234 (NH), 1662 (CONH), 1634 (C N), 1626 (C C); H-NMR (DMSO-
d6) d [ppm]: 2.36 (s, 6H, Ar-CH3), 4.65 (s, 4H, S-CH2), 7.15–7.35 (m,
–
–
–
–
8H, Ar-H), 11.11 (bs, 2H, NH); 13C-NMR (DMSO-d6) d [ppm]: 24.5 (Ar-
d6) d [ppm]: 4.59 (s, 4H, S-CH2), 7.21–7.50 (m, 10H, Ar-H), 11.32 (bs,
2H, NH); 13C-NMR (DMSO-d ) d [ppm]: 38.2 (S-CH ), 105.6 (C C(S)S),
127.3, 128.3, 129.2, 133.1 (aromatic carbons), 151.4 (HNCO), 162.7
–
CH ), 36.3 (S-CH ), 105.7 (C C-(S)S), 123.8, 127.2, 129.4, 137.6
–
(aromatic carbons), 150.3 (HNCO), 160.6 & 164.0 (C2 & C5),
–
–
3
2
6
2
–
–
164.3 (C CS(S)), 166.2 (COC C). Anal. calcd. for C25H20N6O5S2:
–
–
C, 54.74; H, 3.67; N, 15.32. Found: C, 54.65; H, 3.73; N, 15.41.
–
–
(C CS(S)), 163.2 & 167.3 (C & C ), 164.8 (COC C). Anal. calcd.
2
–
–
5
for C23H16N6O3S4: C, 49.99; H, 2.92; N, 15.21. Found: C, 50.09; H,
2.86; N, 15.15.
5-(Bis((5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-
methylthio)methylene)-pyrimidine-2,4,6-(1H,3H,5H)-
trione 5c
5-(Bis((5-p-tolyl-1,3,4-thiadiazol-2-yl)-
methylthio)methylene)pyrimidine-2,4,6-(1H,3H,5H)-trione
Light brown solid in 73% yield; m.p.: 169–1718C; IR (KBr) nmax
7b
Pale yellow solid in 69% yield; m.p.: 154–1568C; IR (KBr) nmax
1
[cmꢁ1]: 3229 (NH), 1657 (CONH), 1631 (C N), 1620 (C C); H-NMR
–
–
–
–
1
[cmꢁ1]: 3231 (NH), 1658 (CONH), 1632 (C N), 1624 (C C); H-NMR
(DMSO-d6) d [ppm]: 4.74 (s, 4H, S-CH2), 7.26–7.45 (m, 8H, Ar-H),
–
–
–
–
11.86 (bs, 2H, NH); 13C-NMR (DMSO-d6) d [ppm]: 37.5 (S-CH2), 104.9
(DMSO-d6) d [ppm]: 2.41 (s, 6H, Ar-CH3), 4.62 (s, 4H, S-CH2), 7.19–
7.38 (m, 8H, Ar-H), 11.20 (bs, 2H, NH); 13C-NMR (DMSO-d6) d [ppm]:
–
(C C(S)S), 124.6, 127.3, 129.3, 133.6 (aromatic carbons), 150.8
–
–
(HNCO), 161.3 & 165.2 (C2 & C ), 161.9 (C CS(S)), 167.3 (COC C).
–
–
Anal. calcd. for C23H14Cl2N6O5S2: C, 46.87; H, 2.39; N, 14.26.
–
–
5
24.6 (Ar-CH3), 37.3 (S-CH2), 105.9 (C C-(S)S), 124.2, 127.6,
–
–
128.2, 136.9 (aromatic carbons), 151.4 (HNCO), 163.5 (C CS(S)),
–
163.9 & 169.3 (C2 & C ), 165.4 (COC C). Anal. calcd. for
Found: C, 46.95; H, 2.43; N,14.18.
–
–
5
C25H20N6O3S4: C, 51.71; H, 3.47; N, 14.47. Found: C, 51.82; H,
3.54; N, 14.56.
5-(Bis((5-phenyl-1,3,4-oxadiazol-2-yl)-
methylthio)methylene)-dihydro-2-thioxopyrimidine-4,6-
(1H,5H)-dione 6a
5-(Bis((5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)-
methylthio)methylene)-pyrimidine-2,4,6-(1H,3H,5H)-trione
Yellow solid in 70% yield; m.p.: 137–1398C; IR (KBr) nmax [cmꢁ1]:
1
3238 (NH), 1655 (CONH), 1639 (C N), 1622 (C C),1495 (C S); H-
–
–
–
–
–
–
7c
White solid in 75% yield; m.p.: 192–1948C; IR (KBr) nmax [cmꢁ1]:
NMR (DMSO-d6) d [ppm]: 4.68 (s, 4H, S-CH2), 7.20–7.50 (m, 10H, Ar-
H), 11.12 (bs, 2H, NH); 13C-NMR (DMSO-d6) d [ppm]: 37.4 (S–CH2),
1
3227 (NH), 1655 (CONH), 1630 (C N), 1621 (C C); H-NMR (DMSO-
–
–
–
–
–
106.2 (C C(S)S), 126.5, 127.6, 128.3, 129.2 (aromatic carbons),
–
–
159.2 & 163.6 (C2 & C ), 164.6 (C CS(S)), 165.2 (COC C), 174.3
d6) d [ppm]: 4.64 (s, 4H, S-CH2), 7.22–7.46 (m, 8H, Ar-H), 11.27 (bs,
2H, NH); 13C-NMR (DMSO-d ) d [ppm]: 39.1 (S-CH ), 105.3 (C C(S)S),
125.1, 126.9, 130.2, 132.9 (aromatic carbons), 152.2 (HNCO), 160.8
–
–
–
–
–
5
6
2
–
(C S). Anal. calcd. for C23H16N6O4S3: C, 51.48; H, 3.01; N, 15.66.
–
Found: C, 51.32; H, 3.04; N, 15.57.
–
–
(C CS(S)), 164.1 & 168.9 (C & C ), 167.2 (COC C). Anal. calcd.
–
for C23H14Cl2N6O3S4: C, 44.45; H, 2.27; N, 13.52. Found: C, 44.52;
–
2
5
H, 2.19; N, 13.63.
5-(Bis((5-p-tolyl-1,3,4-oxadiazol-2-yl)-
methylthio)methylene)-dihydro-2-thioxopyrimidine-4,6-
5-(Bis((5-phenyl-1,3,4-thiadiazol-2-yl)-
methylthio)methylene)-dihydro-2-thioxopyrimidine-4,6-
(1H,5H)-dione 8a
(1H,5H)-dione 6b
White solid in 65% yield; m.p.: 146–1488C; IR (KBr) nmax [cmꢁ1]: 3235
(NH), 1653 (CONH), 1636 (C N), 1620 (C C),1493 (C S); 1H-NMR
–
–
–
–
–
–
White solid in 69% yield; m.p.: 175–1778C; IR (KBr) nmax [cmꢁ1]:
(DMSO-d6) d [ppm]: 2.39 (s, 6H, Ar-CH3), 4.69 (s, 4H, S-CH2), 7.18–
7.40 (m, 8H, Ar-H), 11.37 (bs, 2H, NH); 13C-NMR (DMSO-d6) d [ppm]:
1
3236 (NH), 1664 (CONH), 1638 (C N), 1629 (C C), 1496 (C S); H-
–
–
–
–
–
–
–
24.3 (Ar-CH ), 39.2 (S-CH ), 105.9 (C C-(S)S), 124.1, 127.3, 129.2,
–
–
138.1 (aromatic carbons), 160.2 & 164.9 (C & C ), 165.1 (C CS(S)),
3
2
NMR (DMSO-d6) d [ppm]: 4.70 (s, 4H, S-CH2), 7.30–7.51 (m, 10H, Ar-
H), 11.34 (bs, 2H, NH); 13C-NMR (DMSO-d6) d [ppm]: 37.9 (S-CH2),
–
166.7 (COC C), 172.8 (C S). Anal. calcd. for C25H20N6O4S3: C, 53.18;
2
5
–
–
–
–
H, 3.57; N, 14.88. Found: C, 53.07; H, 3.49; N, 14.73.
–
–
106.4 (C C(S)S), 126.9, 128.6, 129.8, 133.1 (aromatic carbons),
–
–
163.6 (C CS(S)), 165.2 & 168.2 (C & C ), 166.9 (COC C), 174.3
2
–
–
5
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