542
O. AtesË et al. / Il Farmaco 53 (1998) 541±544
bamoic acid in 30 ml of ethanol were re¯uxed on a water
bath for 1 h. Crystals were ®ltered off and recrystallized
from ethanol. Physical data of compounds 5a±n are reported
in Table 1.
1
IR, H NMR and EI mass spectral data of some novel
compounds chosen as prototypes are as follows.
3.2. 5-Phenyl-2-[(N,N-dimethylthiocarbamoylthio)-
phenylacetylamino]-1,3,4-oxadiazole (5a)
IR [n, cm21, KBr]: 3447 (N±H), 3034 (arom. C±H), 2927
(aliph. C±H), 1704 (CyO), 1580, 1547, 1489 (arom. CyC),
1448 (CO±CH), 1381 (C±N, ter. amine), 1252 (N±H and
C±N), 1150 (CyS), 1021, 986 (oxadiazole C±O±C).
1H NMR [400 MHz, d ppm, DMSO-d6]: 3.40 (s, 3H,
CH3), 3.49 (s, 3H, CH3), 5.91 (s, 1H, CH±S), 7.33±7.97
(m, 10H, Harom.), 12.19 (s, 1H, NH).
Scheme 1.
Aromatic aldehyde semicarbazones [11], 5-aryl-2-amino-
1,3,4-oxadiazoles [12], 5-aryl-2-acylamino-1,3,4-oxadia-
zoles [6] and potassium salts of N,N-disubstituted dithiocar-
bamoic acids [7±10] were prepared as previously described.
3.1. 5-Aryl-2-[(N,N-disubstituted thiocarbamoylthio)-
acylamino]-1,3,4-oxadiazoles (5a±n)
MS: m/z (%): 398 (2), 310 (40), 279 (22), 237 (95), 210
(4), 209 (22), 188 (39), 161 (45), 145 (35), 122 (17), 120
(47), 118 (75), 117 (3), 105 (50), 103 (21), 90 (45), 88 (100),
78 (11), 77 (57), 57 (1), 56 (6).
2-[(a-Chloro-a-phenylacetyl/a-bromopropionyl)amino]-
5-phenyl/p-chlorophenyl-1,3,4-oxadiazole (0.005 mol) and
0.005 mol of potassium salt of N,N-disubstituted dithiocar-
3.3. 5-Phenyl-2-[2-(N,N-dimethylthiocarbamoylthio)-
propionylamino]-1,3,4-oxadiazole (5f)
Table 1
Physical constants of compounds 5a±n
IR [n, cm21, KBr]: 3158 (N±H), 3070 (arom. C±H), 2978
(aliph. C±H), 1697 (CyO), 1614, 1584, 1508, 1488 (arom.
CyC), 1450 (CO±CH), 1379 (C±N, ter. amine), 1248
(CyS), 1213 (N±H and C±N), 1038, 968 (oxadiazole
C±O±C).
1H NMR [400 MHz, d ppm, DMSO-d6]: 1.52 (d, J
7:29 Hz, 3H, CH±CH3), 3.31 (s, 3H, N±CH3), 3.37 (s, 3H,
N±CH3), 4.68 (q, 1H, CH±S) 7.13±7.87 (m, 5H, Harom.),
12.06 (s, 1H, NH).
3.4. 5-(p-Chlorophenyl)-2-[(N,N-diethylthiocarbamoyl-
thio)phenylacetylamino]-1,3,4-oxadiazole (5h)
IR [n, cm21, KBr]: 3436 (N±H), 3056 (arom. C±H), 2973,
2932 (aliph. CH), 1727 (CyO), 1607, 1576, 1546, 1485
(arom. CyC), 1452 (CO±CH), 1355 (C±N, ter. amine),
1273 (N±H and C±N), 1206 (CyS), 1047, 983 (oxadiazole
C±O±C).
1H NMR [200 MHz, d ppm, DMSO-d6]: 1.17 (t, 3H,
CH3), 1.23 (t, 3H, CH3), 3.74 (q, 2H, CH2), 3.93 (q, 2H,
CH2), 5.91 (s, 1H, CH±S), 7.38±7.51 (m, 5H, Harom.), 7.65
(d, J 8:40 Hz, 2H, C3,5±H of phenyl bonded to oxadia-
zole), 7.90 (d, J 8:48 Hz, 2H, C2,6±H of phenyl bonded to
oxadiazole), 12.41 (s, 1H, NH).
3.5. 5-(p-Chlorophenyl)-2-[2-(N,N-dimethylthiocarbamoyl-
thio)propionylamino]-1,3,4-oxadiazole (5k)
IR [n, cm21, KBr]: 3463 (N±H), 3139 (arom. C±H), 2870
(aliph. C±H), 1741 (CyO), 1606, 1576, 1499, 1482 (arom.