1
596
H.-Y. SU ET AL.
1
3
5
1
1
7
.78 (s, 1 H), 5.47 (s, 1 H), 2.60 (q, J = 7.2 Hz, 2 H), 1.20 (t, J = 7.2 Hz, 3 H). C NMR: δ =
47.7, 144.6, 143.1, 134.7, 129.9, 128.9, 128.4, 127.7, 127.4, 125.8, 119.5, 109.3, 28.7,
5.5. IR (film): ν = 3028, 2964, 2928, 1642, 1496, 1445, 1265, 1230, 1017, 896, 839, 800,
–
1
+
72, 693 cm . EIMS: m/z (%) = 275 [M ]. Anal. Calcd for C18H17N3: C, 78.52; H, 6.22;
N, 15.26. Found: C, 78.39; H, 6.38; N, 15.15.
1
-(E)-Phenylethenyl-4-(2-methoxyphenoxymethyl)-1,2,3-triazole (4c). White
◦
1
solid, mp 123–124 C. H NMR: δ = 7.96 (s, 1 H), 7.75 (d, J = 14.8 Hz, 1 H), 7.47 (d, J
7.6 Hz, 2 H), 7.41–7.31 (m, 3 H), 7.15 (d, J = 14.8 Hz, 1 H), 7.07 (d, J = 7.6 Hz, 1
=
13
H), 6.97–6.88 (m, 3 H), 5.35 (s, 2 H), 3.88 (s, 3 H). C NMR: δ = 149.6, 147.5, 144.8,
1
33.5, 129.0, 128.8, 126.8, 122.9, 122.0, 121.9, 120.9, 120.3, 114.3, 111.9, 63.1, 55.9. IR
(
KBr): ν = 3153, 3115, 2953, 1654, 1590, 1570, 1503, 1465, 1456, 1439, 1393, 1359,
–
1
1
3
5
325, 1288, 1251, 1177, 1123, 1054, 1026, 1010, 956, 875, 750 cm . EIMS: m/z (%) =
+
07 [M ]. Anal. Calcd for C18H17N3O2: C, 70.34; H, 5.58; N, 13.67. Found: C, 70.20; H,
.74; N, 13.55.
1
-(E)-Phenylethenyl-4-(2-methylphenoxymethyl)-1,2,3-triazole (4d). Pale yellow
◦
1
solid, mp 129–130 C. H NMR: δ = 7.90 (s, 1 H), 7.77 (d, J = 14.4 Hz, 1 H), 7.48 (d, J =
7
.2 Hz, 2 H), 7.41–7.32 (m, 3 H), 7.19–7.13 (m, 3 H), 6.97 (d, J = 8.4 Hz, 1 H), 6.92 (d,
13
J = 14.4 Hz, 1 H), 5.28 (s, 2 H), 2.04 (s, 3 H). C NMR: δ = 156.4, 145.2, 133.5, 130.8,
1
29.0, 128.9, 127.0, 126.9, 126.8, 123.0, 122.1, 121.1, 120.0, 111.5, 62.2, 16.3. IR (KBr):
–
1
ν = 3136, 3096, 2927, 1655, 1493, 1454, 1383, 1350, 1239, 1050, 1021, 950, 752 cm .
+
EIMS: m/z (%) = 291 [M ]. Anal. Calcd for C18H17N3O: C, 74.20; H, 5.88; N, 14.42.
Found: C, 74.03; H, 5.96; N, 14.32.
1
-(E)-Phenylethenyl-4-(2-chlorophenoxymethyl)-1,2,3-triazole (4e). Pale yellow
◦
1
solid, mp 106–107 C. H NMR: δ = 7.98 (s, 1 H), 7.76 (d, J = 14.8 Hz, 1 H), 7.47 (d,
J = 7.2 Hz, 2 H), 7.41–7.32 (m, 4 H), 7.26–7.19 (m, 2 H), 7.15 (d, J = 15.6 Hz, 1 H),
6
1
2
.92–6.89 (m, 1 H), 5.34 (s, 2 H). 13C NMR: δ = 153.7, 144.4, 133.5, 130.4, 129.0, 128.9,
27.9, 126.8, 123.2, 122.9, 122.2, 120.3, 116.2, 114.3, 63.4. IR (KBr): ν = 3104, 3086,
–
1
931, 1654, 1587, 1485, 1388, 1350, 1242, 1161, 1133, 1049, 1018, 969, 856, 750 cm .
+
EIMS: m/z (%) = 311 [M ]. Anal. Calcd for C17H14ClN3O: C, 65.49; H, 4.53; N, 13.48.
Found: C, 65.34; H, 4.68; N, 13.35.
1
-(E)-Phenylethenyl-4-(2-nitrophenoxymethyl)-1,2,3-triazole (4f). Pale yellow
◦
1
solid, mp 134–135 C. H NMR: δ = 8.04 (s, 1 H), 7.87 (dd, J = 8.0, 1.2 Hz, 1 H), 7.76
(
7
1
d, J = 14.8 Hz, 1 H), 7.58–7.54 (m, 1 H), 7.48 (d, J = 7.2 Hz, 2 H), 7.41–7.30 (m, 4 H),
13
.22 (d, J = 14.8 Hz, 1 H), 7.10–7.06 (m, 1 H), 5.42 (s, 2 H). C NMR: δ = 151.4, 143.6,
40.2, 134.3, 133.4, 129.0, 128.8, 126.8, 125.7, 122.8, 122.4, 121.2, 120.7, 115.4, 63.7. IR
(
7
KBr): ν = 3071, 2957, 1658, 1606, 1517, 1347, 1275, 1251, 1168, 1044, 993, 957, 862,
–
1
+
75, 750, 693 cm . EIMS: m/z (%) = 322 [M ]. Anal. Calcd for C17H14N4O3: C, 63.35;
H, 4.38; N, 17.38. Found: C, 63.19; H, 4.56; N, 17.26.
1
-(E)-Phenylethenyl-4-(4-nitrophenoxymethyl)-1,2,3-triazole (4g). Pale yellow
◦
1
solid, mp 149–150 C. H NMR: δ = 8.22–8.19 (m, 2 H), 7.99 (s, 1 H), 7.77 (d, J =
4.8 Hz, 1 H), 7.48 (d, J = 7.6 Hz, 2 H), 7.42–7.33 (m, 3 H), 7.22 (d, J = 14.8 Hz, 1
1
13
H), 7.11–7.07 (m, 2 H), 5.36 (s, 2 H). C NMR: δ = 163.0, 143.1, 141.9, 133.3, 129.0,
1
1
9
28.8, 126.8, 126.0, 122.7, 122.6, 120.6, 114.9, 62.3. IR (KBr): ν = 3080, 2930, 2875, 1654,
607, 1591, 1510, 1495, 1459, 1348, 1297, 1249, 1176, 1153, 1113, 1048, 1018, 1006,
–
1
+
51, 868, 846, 751, 696 cm . EIMS: m/z (%) = 322 [M ]. Anal. Calcd for C17H14N4O3:
C, 63.35; H, 4.38; N, 17.38. Found: C, 63.21; H, 4.53; N, 17.24.
-(E)-Phenylethenyl-4-(2-naphthoxymethyl)-1,2,3-triazole (4h). White solid, mp
1
◦
1
1
58–159 C. H NMR: δ = 7.97 (s, 1 H), 7.97–7.74 (m, 4 H), 7.48–7.44 (m, 3 H), 7.40–7.34