I. Zaki et al.
-
1 1
(
C–N) cm ; H NMR (400 MHz, CDCl ): d = 8.96 (s,
(d, J = 8.4 Hz, 1H, Ar–H), 3.84 (s, 3H, OCH ), 3.79 (s,
3
3
1
3
1
H, NH), 8.06 (d, J = 8.3 Hz, 1H, Ar–H), 7.98 (d,
J = 8.3 Hz, 1H, Ar–H), 7.63–7.34 (m, 7H, Ar–H), 7.09
s, 2H, Ar–H), 6.72 (d, J = 8.9 Hz, 2H, Ar–H), 3.89 (s,
H, 29OCH ), 3.85 (s, 3H, OCH ), 3.74 (s, 3H, OCH )
3H, OCH ), 3.47 (s, 3H, OCH ) ppm;
3
C NMR
3
(101 MHz, CDCl ): d = 160.2, 156.9, 156.8, 156.6,
3
(
150.7, 148.6, 138.5, 134.4, 134.1, 130.8, 129.7, 128.3,
128.2, 127.5, 125.5, 125.1, 122.3, 121.6, 118.8, 111.9,
111.1, 110.8, 110.6, 105.6, 56.1, 55.7, 55.5 ppm; HRMS:
6
3
3
3
1
3
ppm; C NMR (101 MHz, CDCl ): d = 161.4, 157.0,
56.8, 153.5, 134.8, 134.4, 134.2, 133.6, 131.1, 130.1,
3
?
1
1
1
m/z calcd for C H N O ([M?H] ) 481.1870, found
28 25 4 4
29.5, 128.5, 128.3, 127.4, 125.7, 125.3, 122.6, 118.9,
481.1862.
N,5-Bis(3,4-dimethoxyphenyl)-1-(naphthalen-1-yl)-1H-
,2,4-triazole-3-carboxamide (6c, C H N O )
14.2, 97.8, 61.2, 56.3, 55.4 ppm; HRMS: m/z calcd for
?
C H N O ([M?H] ) 511.1976, found 511.1976.
29 27 4 5
1
2
9 27 4 5
N-(3,5-Difluorophenyl)-5-(4-methoxyphenyl)-1-(naph-
thalen-1-yl)-1H-1,2,4-triazole-3-carboxamide
Red crystals (265 mg, 65% yield); m.p.: 89–91 °C
1
(methanol); H NMR (400 MHz, CDCl ): d = 8.94 (s,
3
(
5e, C H F N O )
2
1H, NH), 8.07 (d, J = 8.1 Hz, 1H, Ar–H), 7.98 (d,
J = 8.1 Hz, 1H Ar–H), 7.63–7.41 (m, 6H, Ar–H), 7.18
(dd, J = 8.6, 2.5 Hz, 1H, Ar–H), 7.07–6.98 (m, 2H, Ar–
H), 6.87 (d, J = 8.7 Hz, 1H, Ar–H), 6.66 (d, J = 8.4 Hz,
1H, Ar–H), 3.93 (s, 3H, OCH ), 3.89 (s, 3H, OCH ), 3.80
6 19 2 4 2
Pale brown crystals (277 mg, 70% yield); m.p.: 94–96 °C
(
ethanol); IR (KBr): mꢀ = 3351 (NH), 1691 (C=O), 1589
-
1 1
(
C–N) cm ; H NMR (400 MHz, CDCl ): d = 9.16 (s,
3
1
H), 8.09 (d, J = 8.1 Hz, 1H, Ar–H), 8.01 (d, J = 8.1 Hz,
3
3
1
3
1
H, Ar–H), 7.63–7.50 (m, 4H, Ar–H), 7.47–7.38 (m, 5H,
(s, 3H, OCH ), 3.48 (s, 3H, OCH ) ppm; C NMR
3 3
Ar–H), 6.75 (d, J = 8.9 Hz, 2H, Ar–H), 6.69–6.59 (m, 1H,
(101 MHz, CDCl ): d = 156.9, 150.9, 149.3, 148.8,
3
1
3
Ar–H), 3.77 (s, 3H, OCH ) ppm; C NMR (101 MHz,
146.2, 134.8, 134.4, 131.2, 130.9, 129.7, 128.5, 128.4,
127.5, 125.8, 125.4, 122.6, 121.8, 118.9, 112.1, 111.5,
111.2, 110.9, 104.9, 56.3, 56.2, 56.1, 55.7 ppm; HRMS:
3
CDCl ): d = 164.7, 162.1, 161.8, 161.5, 157.1, 156.3,
3
1
34.3, 131.1, 130.1, 129.4, 128.6, 128.3, 127.5, 125.7,
?
1
25.3, 122.5, 118.7, 114.2, 103.3, 102.9, 99.9, 55.4 ppm;
m/z calcd for C H N O ([M?H] ) 511.1976, found
29 27 4 5
?
HRMS: m/z calcd for C H F N O ([M ? H] )
511.1971.
2
6 19 2 4 2
4
57.1471, found 457.1467.
5-(3,4-Dimethoxyphenyl)-1-(naphthalen-1-yl)-N-(3,4,5-tri-
5
-(3,4-Dimethoxyphenyl)-N-(2-methoxyphenyl)-1-(naph-
methoxyphenyl)-1H-1,2,4-triazole-3-carboxamide
thalen-1-yl)-1H-1,2,4-triazole-3-carboxamide
6a, C H N O )
(6d, C H N O )
3
0 29 4 6
(
Pale brown crystals (237 mg, 55% yield); m.p.: 94–96 °C
2
8 25 4 4
1
Red crystals (280 mg, 73% yield); m.p.: 99–101 °C
(methanol); H NMR (400 MHz, CDCl ): d = 8.94 (s,
3
(
ethanol); IR (KBr): mꢀ = 3332 (NH), 1690 (C=O), 1589
1H, NH), 8.06 (d, J = 8.1 Hz, 1H, Ar–H), 7.98 (d,
J = 8.1 Hz, 1H, Ar–H), 7.73–7.38 (m, 5H, Ar–H), 7.08
(s, 2H, Ar–H), 7.06–6.83 (m, 2H, Ar–H), 6.66 (d,
-
1 1
(
C–N) cm ; H NMR (400 MHz, CDCl ): d = 9.65 (s,
3
1
H, NH), 8.64 (d, J = 7.9 Hz, 1H, Ar–H), 8.07 (d,
J = 7.7 Hz, 1H, Ar–H), 8.00–7.93 (d, J = 7.8 Hz, 1H,
J = 8.4 Hz, 1H, Ar–H), 3.89 (s, 6H, 2OCH ), 3.84 (s,
3
Ar–H), 7.67–7.35 (m, 6H, Ar–H), 7.10–6.91 (m, 4H, Ar–
3H, OCH ), 3.80 (s, 3H, OCH ), 3.47 (s, 3H, OCH ) ppm;
3
3
3
1
3
H), 6.67 (d, J = 8.5 Hz, 1H, Ar–H), 3.93 (s, 3H, OCH ),
3
C NMR (101 MHz, CDCl ): d = 157.1, 157.1, 156.8,
3
1
3
.80 (s, 3H, OCH ), 3.46 (s, 3H, OCH ) ppm; C NMR
3
153.5, 150.9, 148.8, 135.1, 134.7, 134.4, 133.7, 131.1,
129.6, 128.5, 128.4, 127.5, 125.8, 125.4, 122.5, 121.8,
118.8, 111.2, 110.9, 97.8, 61.1, 56.3, 56.1, 55.7 ppm;
3
3
(
101 MHz, CDCl ): d = 148.7, 148.5, 134.3, 130.9, 128.4,
3
1
28.3, 127.4, 125.9, 125.4, 124.3, 122.7, 121.8, 121.3,
?
1
20.5, 111.3, 110.9, 110.1, 55.9, 55.6 ppm; HRMS: m/z
HRMS: m/z calcd for C H N O ([M?H] ) 541.2082,
30 29 4 6
?
calcd for C H N O ([M ? H] ) 481.1870, found
found 541.2100.
2
8 25 4 4
4
81.1863.
N-(3,5-Difluorophenyl)-5-(3,4-dimethoxyphenyl)-1-(naph-
thalen-1-yl)-1H-1,2,4-triazole-3-carboxamide
(6e, C H F N O )
5
-(3,4-Dimethoxyphenyl)-N-(3-methoxyphenyl)-1-(naph-
thalen-1-yl)-1H-1,2,4-triazole-3-carboxamide
6b, C H N O )
2
7
21
2 4 3
(
Brown crystals (264 mg, 68% yield); m.p.: 91–93 °C
2
8 25 4 4
1
Yellow crystals (241 mg, 63% yield); m.p.: 121–123 °C
(ethanol); H NMR (400 MHz, CDCl ): d = 9.21 (s, 1H,
3
(
methanol); IR (KBr): mꢀ = 3336 (NH), 1696 (C=O), 1589
NH), 8.07 (d, J = 8.1 Hz, 1H, Ar–H), 7.98 (d, J = 8.2 Hz,
-
1 1
(
C–N) cm ; H NMR (400 MHz, CDCl ): d = 9.02 (s,
1H, Ar–H), 7.74–7.28 (m, 7H, Ar–H), 7.12–6.87 (m, 2H,
3
1
H, NH), 8.06 (d, J = 8.1 Hz, 1H, Ar–H), 7.98 (d,
Ar–H), 6.73–6.54 (m, 2H, Ar–H), 3.79 (s, 3H, OCH ), 3.47
3
1
(s, 3H, OCH ) ppm; C NMR (101 MHz, CDCl3):
3
J = 8.1 Hz, 1H, Ar–H), 7.66–7.48 (m, 5H, Ar–H),
3
7
7
.47–7.37 (m, 1H, Ar–H), 7.32–7.24 (m, 2H, Ar–H),
.07–6.96 (m, 2H, Ar–H), 6.78–6.68 (m, 1H Ar–H), 6.65
d = 164.5, 164.3, 162.1, 161.9, 151.1, 148.7, 139.8,
134.2, 131.0, 129.3, 128.4, 128.3, 127.4, 125.7, 125.2,
1
23