ꢂꢁꢁꢁ
P. Gao and Y. Wei: Synthesis of 2,5-disubstituted 1,3,4-oxadiazolesꢀ
ꢀ117
2-sec-Butyl-5-phenyl-[1,3,4]oxadiazole (2m)ꢀYield 81%, this
compound was obtained as oil. 1H NMR (CDCl3): δ 8.02 (m, 2H,
CH), 7.47 (m, 3H, CH), 3.07 (m, 1H, CH), 1.88 (m, 1H, CH2), 1.73 (m,
1H, CH2), 1.40 (d, 3H, CH3, J = 7.0Hz), 0.96 (t, 3H, CH3, J = 7 Hz); 13C
NMR (CDCl3): δ 170.2, 164.6, 131.5, 129.0, 125.8, 124.8, 33.2, 27.8, 17.7,
11.5. HR-MS. Calcd for C12H15ClN2O (M+1): m/z 237.0722, found m/z
237.0719.
8.03 (d, 2H, CH, J = 8.5 Hz), 7.52 (d, 2H, CH, J = 8.5 Hz), 7.35 (d, 2H, CH,
J = 8.5 Hz), 2.45 (s, 3H, CH3).
2-(4-Bromophenyl)-5-p-tolyl-[1,3,4]oxadiazole (2t)ꢀYield 91%;
this compound was obtained as white solid, mp 204–206°C ([53],
1
yield 82%; mp 208°C); H NMR (CDCl3): δ 8.03 (m, 4H, CH), 7.69 (m,
2H, CH), 7.34 (m, 2H, CH), 2.45 (s, 3H, CH3).
2-(2-Bromophenyl)-5-(4-methoxyphenyl)-[1,3,4]oxadiazole
2-Heptyl-5-phenyl-[1,3,4]oxadiazole (2n)ꢀYield 75%; this com-
(2u) ꢀYield 87%; this compound was obtained as white solid, mp
1
pound was obtained as oil ([13], yield 95%; oil); H NMR (CDCl3): δ
1
139–141°C; H NMR (CDCl3): δ 8.09 (m, 2H, CH), 8.04 (m, 2H, CH),
8.04 (m, 2H, CH), 7.51 (m, 3H, CH), 2.92 (t, 2H, CH2, J = 7.5Hz), 1.85 (m,
2H, CH2), 1.30–1.45 (m, 8H, CH2), 0.89 (t, 3H, CH3, J = 6.8 Hz).
7.47 (m, 1H, CH), 7.40 (m, 1H, CH), 7.04 (m, 2H, CH), 3.90 (s, 3H, CH3);
13C NMR (CDCl3): δ 165.1, 163.1, 162.6, 134.6, 132.4, 131.7, 128.9, 127.7,
125.4, 121.5, 116.2, 114.6, 55.5. HR-MS. Calcd for C15H11N2O2 (M+1): m/z
331.0009, found m/z 331.0011.
2-o-Tolyl-5-phenyl-[1,3,4]oxadiazole (2o)ꢀYield 94%; this com-
pound was obtained as white solid, mp 96–98°C ([10], yield 63%; mp
96°C); 1H NMR (CDCl3): δ 8.15 (m, 2H, CH), 8.06 (m, 1H, CH), 7.55 (m,
3H, CH), 7.45 (m, 1H, CH), 7.37 (m, 2H, CH), 2.79 (s, 3H, CH3).
2-(3-Phenoxyphenyl)-5-o-tolyl-[1,3,4]oxadiazole (2v)ꢀYield 89%;
1
this compound was obtained as white solid, mp 98–100°C; H NMR
(CDCl3): δ 8.02 (m, 1H, CH), 7.87 (m, 1H, CH), 7.77 (m, 1H, CH), 7.49 (t,
1H, CH, J = 8.0 Hz), 7.33–7.45 (m, 5H, CH), 7.17 (m, 2H, CH), 7.08 (m,
2H, CH); 13C NMR (CDCl3): δ 165.0, 163.7, 158.1, 156.4, 138.5, 131.9, 130.6,
130.1, 129.0, 126.2, 125.5, 124.1, 122.9, 121.8, 121.6, 119.4, 116.8, 22.2. HR-
MS. Calcd for C21H16N2O2 (M+1): m/z 329.1215, found m/z 329.1214.
2,5-Bis-(4-chlorophenyl)-[1,3,4]oxadiazole (2p)ꢀYield 89%; this
compound was obtained as white solid, mp 248–250°C ([20], yield
78%; mp 250–251°C); 1H NMR (CDCl3): δ 8.08 (d, 4H, CH, J = 8.5 Hz),
7.53 (d, 4H, CH, J = 8.5 Hz).
2,5-Di-p-tolyl-[1,3,4]oxadiazole (2q)ꢀYield 92%; this compound
was obtained as white solid, mp 172–174°C ([24], yield 72%; mp
178°C); 1H NMR (CDCl3): δ 8.03 (d, 4H, CH, J = 8.0 Hz), 7.33 (d, 4H, CH,
J = 8.0 Hz), 2.44 (s, 6H, CH3).
2-(4-Chlorophenyl)-5-ethyl-[1,3,4]oxadiazole (2w)ꢀYield 77%;
this compound was obtained as white solid, mp 90–92°C ([14], yield
90%; mp 93–94°C); 1H NMR (CDCl3): δ 7.98 (d, 2H, CH, J = 8.5 Hz), 7.48
(d, 2H, CH, J = 8.5 Hz), 2.96 (q, 2H, CH2, J = 8.0 Hz), 1.45 (t, 3H, CH3,
J = 8.0 Hz).
2,5-Bis-(4-methoxyphenyl)-[1,3,4]oxadiazole (2r)ꢀYield 90%;
this compound was obtained as white solid, mp 158–160°C ([20],
yield 83%; mp 158–160°C); 1H NMR (CDCl3): δ 8.06 (d, 4H, CH, J = 8.8
Hz), 7.03 (d, 4H, CH, J = 8.8 Hz), 3.90 (s, 6H, CH3).
2-Benzyl-5-(2-furyl)-[1,3,4]oxadiazole (2x)ꢀYield 83%; this com-
pound was obtained as white solid, mp 149–150°C ([12], yield 62%;
mp 151°C); 1H NMR (CDCl3): δ 7.59 (m, 1H, CH), 7.34 (m, 4H, CH), 7.30
(m, 1H, CH), 7.10 (m, 1H, CH), 6.55 (m, 1H, CH), 4.25 (s, 2H, CH2).
2-(4-Chlorophenyl)-5-p-tolyl-[1,3,4]oxadiazole (2s)ꢀYield 88%;
this compound was obtained as white solid, mp 204–206°C ([24],
yield 65%; mp 204°C); 1H NMR (CDCl3): δ 8.09 (d, 2H, CH, J = 8.5 Hz),
Received October 29, 2012; accepted January 5, 2013; previously
published online March 14, 2013
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