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2897
C7H, J=7.51 Hz), 7.31–7.25 (2H, m, C4H and m-proton
.
to CF3). Anal. calcd for C19H12F3N3OS H2SO4: C,
47.01; H, 2.90; N, 8.66; S, 13.21. Found: C, 47.52; H,
3.26; N, 8.53; S, 11.95.
2-(N-Acetyl-N-p-chlorophenylamino)-5-(3-acetyloxy-2-
naphthyl)-1,3,4-thiadiazole
(3e).
Creamysctrayl
(55.5%); mp 222–226 ꢃC; IR: 3056, 1761, 1690, 1628,
1
1599, 1487, 1436, 897, 748, 843, 621 cmꢀ1. H NMR, d
ppm: 8.69 (1H, s, C1H), 8.14 (1H, d, C8H, J=8.12 Hz),
7.97 (1H, d, C5H, J=7.25 Hz), 7.90 (1H, s, C4H), 7.67–
7.56 (6H, m, C6H, C7H and C6H4), 2.40 (3H, s,
NCOCH3), 2.07 (3H, s, OCOCH3). Anal. calcd for
C22H16ClN3O3S: C, 60.34; H, 3.68; N, 9.60; S, 7.32.
Found: C, 59.75; H, 3.74; N, 9.14; S, 7.36.
General procedure for preparation of 2-(N-alkyl/aryl-N-
acetylamino)-5-(3-acetyloxy-2-naphthyl)-1,3,4-thiadiazoles
(3a–i)
A mixture of appropriate thiadiazole (0.001 mol) 2a–i in
5 mL acetic anhydride was heated under reflux 90 min.
Distilled water was added to the reaction mixture and
allowed to cool. The resulting precipitate was filtered
and washed with distilled water. The residue was purified
byrecrystallization from ethanol.
2-(N-Acetyl-N-p-fluorophenylamino)-5-(3-acetyloxy-2-
naphthyl)-1,3,4-thiadiazole (3f). Yellow crystal (36.6%);
mp 223 ꢃC; IR: 3066, 1763, 1686, 1628, 1598, 1507,
1
1435, 897, 747, 842, 622 cmꢀ1. H NMR, d ppm: 8.69
(1H, s, C1H), 8.13 (1H, d, C8H, J=8.55 Hz), 7.97 (1H,
d, C5H, J=7.25 Hz), 7.90 (1H, s, C4H), 7.71–7.56 (4H,
m, C6H, C7H and m-protons to F), 7.44 (2H, t, o-protons
to F, J=8.75 Hz), 2.40 (3H, s, NCOCH3), 2.06 (3H, s,
OCOCH3). Anal. calcd for C22H16FN3O3S: C, 62.70; H,
3.83; N, 9.97. Found: C, 62.56; H, 3.77; N, 9.42.
2-(N-Acetyl-N-ethylamino)-5-(3-acetyloxy-2-naphthyl)-
1,3,4-thiadiazole (3a). Creamycrsytal (50.1%); mp
169 ꢃC; IR: 3033–2982, 1768, 1668, 1628, 1599, 1508,
1438, 897, 744, 622 cmꢀ1. 1H NMR, d ppm: 8.72 (1H, s,
C1H), 8.14 (1H, d, C8H, J=7.94 Hz), 7.97 (1H, d, C5H,
J=7.91 Hz), 7.89 (1H, s, C4H), 7.68–7.56 (2H, m, C6H
and C7H), 4.31 (2H, q, CH2), 2.48 (3H, s, NCOCH3,
with DMSO), 2.40 (3H, s, OCOCH3), 1.38 (3H, t, CH3).
Anal. calcd for C18H17N3O3S: C, 60.83; H, 4.82; N,
11.82. Found: C, 60.18; H, 4.23; N, 12.47.
2-(N-Acetyl-N-m-fluorophenylamino)-5-(3-acetyloxy-2-
(3g).
naphthyl)-1,3,4-thiadiazole
Creamysctrayl
(86.7%); mp 169 ꢃC; IR: 3058, 1766, 1689, 1597, 1486,
1438, 903, 753, 823, 618 cmꢀ1. H NMR, d ppm: 8.82
1
(1H, s, C1H), 8.26 (1H, d, C8H, J=7.96 Hz), 8.10 (1H,
d, C5H, J=8.06 Hz), 8.03 (1H, s, C4H), 7.80–7.70 (4H,
m, C6H, o- and m-protons of phenyl to NCOCH3),
7.62–7.54 (2H, m, C7H and p-proton of phenyl to
NCOCH3), 2.53 (3H, s, NCOCH3), 2.20 (3H, s,
OCOCH3). Anal. calcd for C22H16FN3O3S. H2O: C,
60.13; H, 4.13; N, 9.56; S, 7.30. Found: C, 59.95; H,
3.51; N, 9.30; S, 6.80.
2-(N-Acetyl-N-phenethylamino)-5-(3-acetyloxy-2-naph-
thyl)-1,3,4-thiadiazole (3b). Creamycrystal (55.5%); mp
129 ꢃC; IR: 3052, 1768, 1681, 1626, 1597, 1468, 1442,
1
901, 741, 705, 620 cmꢀ1. H NMR, d ppm: 8.70 (1H, s,
C1H), 8.07 (1H, d, C8H, J=7.83 Hz), 7.90 (1H, d, C5H,
J=7.86 Hz), 7.83 (1H, s, C4H), 7.59–7.51 (2H, m, C6H,
C7H), 7.28–7.17 (5H, m, C6H5), 4.38 (2H, t, CH2–
NCOCH3), 3.05 (2H, t, CH2–C6H5), 2.33 (3H, s,
NCOCH3), 2.20 (3H, s, OCOCH3). Anal. calcd for
C24H21N3O3S: C, 66.80; H, 4.91; N, 9.74; S, 7.43.
Found: C, 67.43; H, 4.78; N, 9.72; S, 7.01.
2-(N-Acetyl-N-p-methoxyphenylamino)-5-(3-acetyloxy-2-
naphthyl)-1,3,4-thiadiazole (3h). Yellow crystal (88.5%);
mp 215 ꢃC; IR: 3054, 2933, 2839, 1762, 1686, 1628,
1
1600, 1508, 1433, 896, 748, 840, 624 cmꢀ1. H NMR, d
2-(N-Acetyl-N-phenylamino)-5-(3-acetyloxy-2-naphthyl)-
1,3,4-thiadiazole (3c). Yellow crystal (70.7%); mp 185ꢃC;
IR: 3057, 1757, 1686, 1629, 1592, 1489, 1433, 897, 754, 703,
620 cmꢀ1. 1H NMR, d ppm: 8.82 (1H, s, C1H), 8.26 (1H, d,
C8H, J=7.92 Hz), 8.10 (1H, d, C5H, J=7.98 Hz), 8.03
(1H, s, C4H), 7.77–7.71 (7H, m, C6H, C7H and C6H5), 2.53
(3H, s, NCOCH3), 2.17 (3H, s, OCOCH3). Anal. calcd for
C22H17N3O3S: C, 65.49; H, 4.25; N, 10.41; S, 7.95.
Found: C, 65.67; H, 3.65; N, 10.06; S, 7.33.
ppm: 8.81 (1H, s, C1H), 8.26 (1H, d, C8H, J=7.88 Hz),
8.10 (1H, d, C5H, J=7.97 Hz), 8.02 (1H, s, C4H), 7.79–
7.70 (2H, m, C6H and C7H), 7.62 (2H, d, m-protons to
OCH3, J=8.76 Hz), 7.26 (2H, d, o-protons to OCH3,
J=8.80 Hz), 3.98 (3H, s, CH3), 2.52 (3H, s, NCOCH3),
2.18 (3H, s, OCOCH3). Anal. calcd for C23H19N3O4S:
C, 63.73; H, 4.42; N, 9.69; S, 7.40. Found: C, 63.09; H,
3.91; N, 9.32; S, 6.94.
2-(N-Acetyl-N-p-methylphenylamino)-5-(3-acetyloxy-2-
naphthyl)-1,3,4-thiadiazole (3i). Creamycrystal (94.0%);
mp 208 ꢃC; IR: 3055, 2920, 1764, 1686, 1628, 1598,
2-(N-Acetyl-N-p-bromophenylamino)-5-(3-acetyloxy-2-
naphthyl)-1,3,4-thiadiazole
(3d).
Creamysctrayl
(59.5%); mp 227 ꢃC; IR: 3066, 1757, 1686, 1628, 1600,
1509, 1435, 892, 745, 840, 622 cmꢀ1. H NMR, d ppm:
1
1
1487, 1433, 896, 754, 847, 620 cmꢀ1. H NMR, d ppm:
8.81 (1H, s, C1H), 8.26 (1H, d, C8H, J=7.94 Hz), 8.10
(1H, d, C5H, J=8.00 Hz), 8.02 (1H, s, C4H), 7.79–7.70
(2H, m, C6H and C7H), 7.58 (2H, d, m-protons to CH3,
J=8.24 Hz), 7.53 (2H, d, o-protons to CH3,
J=8.20 Hz), 2.55 (3H, s, CH3), 2.52 (3H, s, NCOCH3),
2.17 (3H, s, OCOCH3). Mass (EI) m/z (relative inten-
sity): 187 (37), 169 (13), 158 (59), 141 (21), 140 (27), 128
(53), 126 (15), 115 (96), 114 (57), 102 (89), 91 (82), 89
(45), 77 (93), 76 (15), 65 (55), 63 (42), 58 (100). Anal.
calcd for C23H19N3O3S: C, 66.17; H, 4.59; N, 10.06; S,
7.68. Found: C, 66.08; H, 4.32; N, 9.69; S, 7.07.
8.69 (1H, s, C1H), 8.14 (1H, d, C8H, J=7.88 Hz), 7.97
(1H, d, C5H, J=8.05 Hz), 7.90 (1H, s, C4H), 7.82 (2H,
d, o-protons to Br, J=8.67 Hz), 7.71–7.54 (4H, m, C6H,
C7H and m-protons to Br), 2.40 (3H, s, NCOCH3), 2.07
(3H, s, OCOCH3). Mass (EI) m/z (relative intensity):
187 (20), 169 (25), 158 (79), 155 (12), 141 (39), 140 (52),
128 (23), 126 (22), 115 (93), 114 (81), 102 (24), 89 (21),
77 (23), 76 (44), 65 (20), 63 (100), 58 (35). Anal. calcd
for C22H16BrN3O3S: C, 54.78; H, 3.34; N, 8.71; S, 6.65.
Found: C, 54.60; H, 3.48; N, 8.47; S, 6.90.