POKHODYLO et al.
420
3-{5-[1-(2-Methoxyphenyl)-5-methyl-1H-1,2,3-
%: C 49.55; H 3.08; N 20.10. C17H13BrN6O2. Calculat-
ed, %: C 49.41; H 3.17; N 20.34.
triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine (VIIi).
1
Yield 67%, mp 156°C. H NMR spectrum, δ, ppm:
3-{5-[5-Methoxymethyl-1-(3-trifluoromethyl-
2.55 s (3H, Me), 3.89 s (3H, OMe), 7.22 t (1H, 5′-H,
J = 7.6 Hz), 7.35 d (1H, 3′-H, J = 8.4 Hz), 7.51 d (1H,
6′-H, J = 7.6 Hz), 7.64 m (2H, 4′-H, 5-H), 8.49 d (1H,
4-H, J = 8.0 Hz), 8.80 d (1H, 6-H, J = 4.8 Hz), 9.30 s
(1H, 2-H). Found, %: C 60.82; H 4.13; N 25.27.
C17H14N6O2. Calculated, %: C 61.07; H 4.22; N 25.14.
phenyl)-1H-1,2,3-triazol-4-yl]-1,3,4-oxadiazol-2-yl}-
1
pyridine (VIIo). Yield 77%, mp 117°C. H NMR
spectrum, δ, ppm: 3.30 s (3H, Me), 4.96 s (2H, CH2),
7.66 d.d (1H, 5-H, J = 4.8, 7.8 Hz), 7.93 t (1H, 5′-H,
J = 8.0 Hz), 7.98 d (1H, 6′-H, J = 8.0 Hz), 8.12 d
(1H, 4′-H, J = 8.0 Hz), 8.16 s (1H, 2′-H), 8.50 d (1H,
4-H, J = 7.6 Hz), 8.81 d (1H, 6-H, J = 4.8 Hz), 9.32 s
(1H, 2-H). Found, %: C 53.61; H 2.97; N 20.84.
C18H13F3N6O2. Calculated, %: C 53.74; H 3.26;
N 20.89.
3-{5-[1-(3-Methoxyphenyl)-5-methyl-1H-1,2,3-
triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine (VIIj).
1
Yield 82%, mp 169°C. H NMR spectrum, δ, ppm:
2.75 s (3H, Me), 3.90 s (3H, OMe), 7.16–7.20 m (2H,
4′-H, 6′-H), 7.23 s (1H, 2′-H), 7.54 t (1H, 5′-H, J =
8.0 Hz), 7.62–7.66 m (1H, 5-H), 8.48 d (1H, 4-H, J =
7.8 Hz), 8.79 d (1H, 6-H, J = 4.0 Hz), 9.29 s (1H, 2-H).
Found, %: C 60.92; H 4.17; N 24.90. C17H14N6O2. Cal-
culated, %: C 61.07; H 4.22; N 25.14.
4-[5-(5-Methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-
1,3,4-oxadiazol-2-yl]pyridine (VIIp). Yield 92%,
1
mp 190°C. H NMR spectrum, δ, ppm: 2.73 s (3H,
Me), 7.62–7.70 m (5H, C6H5), 8.03 d (2H, 3-H, 5-H,
J = 5.8 Hz), 8.84 d (2H, 2-H, 6-H, J = 5.8 Hz). Found,
%: C 63.29; H 3.88; N 27.36. C16H12N6O. Calculated,
%: C 63.15; H 3.97; N 27.62.
3-{5-[1-(4-Chlorophenyl)-5-ethyl-1H-1,2,3-
triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine (VIIk).
1
Yield 93%, mp 104°C. H NMR spectrum, δ, ppm:
4-{5-[1-(2-Chlorophenyl)-5-methyl-1H-1,2,3-
1.24 t (3H, Me, J = 7.4 Hz), 3.15 q (2H, CH2, J =
7.4 Hz), 7.66 d.d (1H, 5-H, J = 4.8, 8.0 Hz), 7.70 s
(4H, C6H4), 8.48 d (1H, 4-H, J = 8.0 Hz), 8.79 d (1H,
6-H, J = 4.8 Hz), 9.30 s (1H, 2-H). Found, %: C 57.69;
H 3.60; N 23.67. C17H13ClN6O. Calculated, %:
C 57.88; H 3.71; N 23.82.
triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine (VIIq).
1
Yield 82%, mp 197°C. H NMR spectrum, δ, ppm:
2.57 s (3H, Me), 7.66–7.81 m (4H, C6H4), 8.04 d (2H,
3-H, 5-H, J = 4.8 Hz), 8.85 d (2H, 2-H, 6-H, J = 4.8 Hz).
Found, %: C 56.47; H 3.12; N 24.66. C16H11ClN6O.
Calculated, %: C 56.73; H 3.27; N 24.81.
3-[5-(5-Isopropyl-1-phenyl-1H-1,2,3-triazol-4-
yl)-1,3,4-oxadiazol-2-yl]pyridine (VIIl). Yield 78%,
4-{5-[1-(2-Methoxyphenyl)-5-methyl-1H-1,2,3-
1
triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine (VIIr).
mp 165°C. H NMR spectrum, δ, ppm: 1.43 d (6H,
1
Yield 69%, mp 175°C. H NMR spectrum, δ, ppm:
Me, J = 6.8 Hz), 3.37–3.47 m (1H, CH), 7.57–7.73 m
(6H, C6H5, 5-H), 8.48 d (1H, 4-H, J = 7.2 Hz), 8.80 d
(1H, 6-H, J = 4.0 Hz), 9.30 s (1H, 2-H). Found, %:
C 65.16; H 4.72; N 25.09. C18H16N6O. Calculated, %:
C 65.05; H 4.85; N 25.29.
2.54 s (3H, Me), 3.87 s (3H, OMe), 7.20 t (1H, 5′-H,
J = 7.6 Hz), 7.34 d (1H, 3′-H, J = 7.6 Hz), 7.50 d (1H,
6′-H, J = 7.6 Hz), 7.65 t (1H, 4′-H, J = 7.6 Hz), 8.04 d
(2H, 3-H, 5-H, J = 4.8 Hz), 8.84 d (2H, 2-H, 6-H,
J = 4.8 Hz). Found, %: C 60.78; H 4.17; N 25.31.
C17H14N6O2. Calculated, %: C 61.07; H 4.22; N 25.14.
3-[5-(5-Methoxymethyl-1-phenyl-1H-1,2,3-tri-
azol-4-yl)-1,3,4-oxadiazol-2-yl]pyridine (VIIm).
1
4-{5-[1-(3-Methoxyphenyl)-5-methyl-1H-1,2,3-
Yield 76%, mp 144°C. H NMR spectrum, δ, ppm:
triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine (VIIs).
3.40 s (3H, Me), 4.90 s (2H, CH2), 7.64–7.78 m (6H,
C6H5, 5-H), 8.50 d (1H, 4-H, J = 8.0 Hz), 8.81 d (1H,
6-H, J = 4.4 Hz), 9.31 s (1H, 2-H). Found, %: C 60.78;
H 4.27; N 24.97. C17H14N6O2. Calculated, %: C 61.07;
H 4.22; N 25.14.
1
Yield 81%, mp 178°C. H NMR spectrum, δ, ppm:
2.73 s (3H, Me), 3.89 s (3H, OMe), 7.16–7.24 m (3H,
2′-H, 4′-H, 5′-H), 7.56 t (1H, 6′-H, J = 8.0 Hz), 8.03 d
(2H, 3-H, 5-H, J = 5.2 Hz), 8.84 d (2H, 2-H, 6-H,
J = 5.2 Hz). Found, %: C 60.94; H 4.10; N 25.03.
C17H14N6O2. Calculated, %: C 61.07; H 4.22; N 25.14.
3-{5-[1-(4-Bromophenyl)-5-methoxymethyl-1H-
1,2,3-triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine
1
(VIIn). Yield 89%, mp 157°C. H NMR spectrum, δ,
4-{5-[1-(4-Chlorophenyl)-5-ethyl-1H-1,2,3-
ppm: 3.39 s (3H, Me), 4.92 s (2H, CH2), 7.67 t (1H,
5-H, J = 4.8 Hz), 7.74 d (2H, m-H, J = 8.0 Hz), 7.83 d
(2H, o-H, J = 8.0 Hz), 8.49 d (1H, 4-H, J = 7.6 Hz),
8.81 d (1H, 6-H, J = 4.8 Hz), 9.30 s (1H, 2-H). Found,
triazol-4-yl]-1,3,4-oxadiazol-2-yl}pyridine (VIIt).
Yield 95%, mp 180°C. H NMR spectrum, δ, ppm:
1.20 t (3H, Me, J = 7.2 Hz), 3.13 q (2H, CH2, J =
7.2 Hz), 7.71 s (4H, C6H4), 8.03 d (2H, 3-H, 5-H, J =
1
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 3 2010