for 5 min and was irradiated by microwave for 1 min using 630 W (A kitchen-type microwave was used in all
experiments). The reaction mixture was grinded in a mortar and pestle until a fine, homogeneous, powder is
obtained. Homogeneous mixture was chromatographed on silica gel (Hexane:EtOAc=95:5) to give pure
product 0.89 g (91 %). mp 143-145°C (ethanol); IR (KBr): 3050, 2980, 1660, 1649 cm-1; 1H-NMR, δH (CDCl3,
13
TMS): 2.68 (s, 3H), 7.39-8.05 (m, 4H): C-NMR, δc (CDCl3, TMS): 12.31, 125.34, 127.4, 128.52, 130.10,
131.08, 134.89, 167.37, 176.78; MS m/z: 196 (M++2, 20), 194 (M+, 60), 153 (100), 125, 90, 43 (80). Anal.
Calcd for C9H7N2OCl: C, 55.54; H, 3.63; N, 14.38. Found: C, 55.22; H, 3.82; N, 14.40.
3-(p-Chlorophenyl)-5-methyl-1, 2, 4-oxadiazole (3c) :
This oxadiazole was prepared in the general way and had mp 140-143°C (ethanol). IR (KBr): 3030, 2891,
1674, 1653 cm-1; 1H-NMR, δH (CDCl3, TMS): 2.63 (s, 3H), 7.44 (dd, 2H, J=8 Hz and J=2 Hz), 7.98 (dd, 2H,
J=8 Hz and J=2 Hz): 13C-NMR, δc (CDCl3, TMS): 12.33, 125.32, 128.62, 129.14, 137.25, 167.59, 176.70; MS
m/z: 196 (M++2, 30), 194 (M+, 100), 153 (75), 125, 90, 43 (65). Anal. Calcd for C9H7N2OCl: C, 55.54; H, 3.63;
N, 14.38. Found: C, 55.28; H, 3.76; N, 14.24.
3-(2, 4-Dichlorophenyl)-5-methyl-1, 2, 4-oxadiazole (3d) :
This oxadiazole was prepared in the general way and had mp 150-152° C (ethanol). IR (KBr): 3010, 2931,
1660, 1640 cm-1; 1H-NMR, δH (CDCl3, TMS): 2.67 (s, 3H), 7.36 (dd, 1H, J=8 Hz and J=2 Hz), 7.55 (d, 1H, J=2
Hz), 7.86 (d, 1H, J=8 Hz); 13C-NMR, δc (CDCl3, TMS): 12.35, 124.73, 127.35, 130.87, 132.41, 134.26,
137.24, 166.58, 176.26; MS m/z: 230 (M++2, 40), 228 (M+, 65), 187 (73), 124 (60), 43 (100). Anal. Calcd for
C9H6N2OCl2: C, 47.19; H, 2.64; N, 12.23. Found: C, 46.90; H, 2.85; N, 12.20.
3-(4-Chlorophenylmethyl)-5-phenyl-1, 2, 4-oxadiazole (3e):
This oxadiazole was prepared in the general way and had mp 76-78° C (ethanol). IR (KBr): 3020, 2910, 1655,
1635 cm-1; 1H-NMR, δH (CDCl3, TMS): 4.10 (s, 2H), 7.28-7.35 (m, 4H), 7.46-7.55 (m, 3H), 8.09 (d, 2H, J=8
13
Hz); C-NMR, δc (CDCl3, TMS): 31.73, 124.02, 128.02, 128.97, 129.05, 129.23, 130.33, 131.10, 132.70,
132.97, 133.94, 169.63, 175.81. Anal. Calcd for C15H11N2OCl: C, 66.55; H, 4.10; N, 10.35. Found: C, 66.38;
H, 4.36; N, 9.89.
3-(2-Phenylvinyl)-5-methyl-1, 2, 4-oxadiazole (3f) :
This oxadiazole was prepared in the general way and had mp 131-133°C (ethanol). IR (KBr): 3040, 2970,
1677, 1652, 1610 cm-1; 1H-NMR, δH (CDCl3, TMS): 2.30 (s, 3H), 6.64 (d, 1H, J=16 Hz), 7.31-7.47 (m, 6H);
13C-NMR, δc (CDCl3, TMS): 27.20, 126.86, 127.98, 130.22, 134.15, 143.06, 197.93; MS m/z: 186 (M+, 20),
149 (50), 128 (45), 77 (32), 43 (100). Anal. Calcd for C16H12N2O. C, 77.40; H, 4.87; N, 11.29. Found: C,
77.21; H, 4.65; N, 10.96.
3-Cyclohexyl-5-phenyl-1, 2, 4-oxadiazole (3g):
This oxadiazole was prepared in the general way and had mp 159-161°C (ethanol). IR (KBr): 3072, 2931,
1663, 1643 cm-1; 1H-NMR, δH (CDCl3, TMS): 1.20 (tt, 1H, J=13 Hz and J=3 Hz), 1.21 (tq, 2H, J=13 Hz and