1
88 Ming et al.
ꢁ
N-(2 -Hydroxyethyl)-4-vinyl-1H-1,2,3-triazole
CDCl3): δ = 8.42 (d, J = 8.8 Hz, 2H), 8.00 (d, J =
8.8 Hz, 2H), 7.69 (s, 1H), 6.80 (dd, J = 18.0, 11.2 Hz,
1H), 6.02 (d, J = 18.0 Hz, 1H), 5.51 (d, J = 11.2 Hz,
1
(
5e). Colorless oil ([24]); H NMR (400 MHz,
CDCl3): δ = 7.60 (s, 1H), 6.60 (dd, J = 18.8, 11.2 Hz,
1
3
1
1
2
1
H), 5.81 (d, J = 18.8 Hz, 1H), 5.30 (d, J = 11.2 Hz,
1H); C NMR (100 MHz, CDCl3): δ = 151.3, 149.1,
141.3, 130.0, 126.4, 125.7, 120.5, 117.1; IR (KBr):
ν = 3121, 1637, 1606, 1529, 1496, 1455, 1350, 1239,
H), 4.61 (t, J = 9.2 Hz, 2H), 4.06 (t, J = 9.2 Hz, 2H),
1
3
.70 (s, 1H); C NMR (100 MHz, CDCl3): δ = 145.6,
–1
25.3, 121.6, 116.0, 60.5, 52.3.
1073, 993, 919, 775, 730 cm ; Calcd for C10H8N4O2:
C 55.55, H 3.73, N 25.91; found: C 55.43, H 3.84,
N 25.99.
Methyl
3-(4-vinyl-1,2,3-triazol-1-yl)propanoate
1
(
5f). Colorless oil ([25]); H NMR (400 MHz,
CDCl3): δ = 7.60 (s, 1H), 6.67 (dd, J = 18.8, 11.2 Hz,
1-(p-Methoxyphenyl)-4-vinyl-1H-1,2,3-triazole
(5l). White solid, mp 66–67°C; H NMR (400 MHz,
1
1
H), 5.83 (d, J = 18.8 Hz, 1H), 5.33 (d, J = 11.2 Hz,
H), 4.61 (t, J = 12.4 Hz, 2H), 3.65 (s, 3 H), 2.95
1
CDCl3): δ = 7.65 (s, 1H), 7.55 (d, J = 8.4 Hz, 2H),
6.94 (d, J = 8.4 Hz, 2H), 6.71 (dd, J = 18.8, 11.2 Hz,
1H), 5.94 (d, J = 18.8 Hz, 1 H), 5.43 (d, J = 11.2 Hz,
1
3
(
t, J = 12.4 Hz, 2H); C NMR (100 MHz, CDCl3):
δ = 171.2, 146.3, 125.6, 121.4, 116.2, 52.4, 45.6, 34.6.
1
3
1
H), 3.79 (s, 3H); C NMR (100 MHz, CDCl3): δ =
3
-(4-vinyl-1,2,3-triazol-1-yl)propionic acid (5g).
159.7, 148.5, 130.2, 129.7, 125.7, 121.7, 116.7, 114.3,
1
Colorless oil ([25]); H NMR (400 MHz, CDCl3):
55.6; IR (KBr): ν = 3071, 2926, 2864, 1641, 1545,
–1
δ = 11.1 (s, 1 H), 7.61 (s, 1 H), 6.70 (dd, J = 18.4,
1496, 1458, 1378, 1221, 996, 910, 826, 720 cm ;
Anal. Calcd for C11H11N3O: C 65.66, H 5.51, N 20.88;
found: C 65.52 H, 5.63, N 20.99.
1
1
1
1
0.8 Hz, 1H), 5.82 (d, J = 18.4 Hz, 1H), 5.34 (d, J =
0.8 Hz, 1H), 4.42 (t, J = 12.8 Hz, 2H), 2.45 (t, J =
1
3
2.8 Hz, 2H); C NMR (100 MHz, CDCl3): δ = 176.2,
46.2, 125.0, 120.8, 116.4, 49.2, 30.4.
1-(m-Methylphenyl)-4-vinyl-1H-1,2,3-triazole
1
(
5m). Yellow oil; H NMR (400 MHz, CDCl3):
1
-Phenyl-4-vinyl-1H-1,2,3-triazole (5h). White
δ = 7.70 (s, 1H), 7.57 (s, 1H), 7.45 (d, J = 7.6 Hz,
1H), 7.34 (d, J = 8.0 Hz, 1H), 7.21 (d, J =
7.2 Hz, 1H), 6.73 (dd, J = 18.4, 10.8 Hz, 1H), 5.93
(d, J = 18.4 Hz, 1H), 5.44 (d, J = 10.8 Hz, 1H), 2.40
1
solid, mp 41–42°C ([29]); H NMR (400 MHz,
CDCl3): δ = 7.92 (s, 1H), 7.71 (d, J = 7.4 Hz, 2H),
7
6
1
.53 (t, J = 15.5 Hz, 2H), 7.43 (t, J = 8.1 Hz, 1H),
1
3
.78 (dd, J = 18.4, 11.2 Hz, 1H), 5.98 (d, J = 18.4 Hz,
(s, 3H); C NMR (100 MHz, CDCl3): δ = 148.8, 139.8,
136.8, 130.6, 129.5, 128.9, 126.0, 121.5, 117.7, 116.8,
20.9; IR (film): ν = 3114, 3069, 2925, 2872, 1639,
1
3
H), 5.40 (d, J = 11.2 Hz, 1H); C NMR (100 MHz,
CDCl3): δ = 148.6, 129.7, 128.6, 125.8, 125.2, 120.2,
–1
1
18.1, 116.5.
1550, 1496, 1437, 1376, 1224, 996, 865, 694 cm ;
Calcd for C11H11N3: C 71.33, H 5.99, N 22.69; found:
C 71.23, H 6.11, N 22.81.
1
-(o-Chlorophenyl)-4-vinyl-1H-1,2,3-triazole (5i).
1
Yellow oil; H NMR (400 MHz, CDCl3): δ = 7.77
(
s, 1H), 7.73 (d, J = 7.2 Hz, 1H), 7.49–7.42 (m, 2H),
1-(o-Methylphenyl)-4-vinyl-1H-1,2,3-triazole
1
7
1
1
1
.34 (t, J = 6.8 Hz, 1H), 6.77 (dd, J = 18.8, 10.8 Hz,
(5n). Yellow oil; H NMR (400 MHz, CDCl3):
H), 5.95 (d, J = 18.8 Hz, 1H), 5.49 (d, J = 10.8 Hz,
δ = 7.70 (s, 1H), 7.44–7.31 (m, 3H), 7.21 (d, J =
8.0 Hz, 1H), 6.86 (dd, J = 18.8, 10.8 Hz, 1H), 5.93
(d, J = 18.8 Hz, 1H), 5.48 (d, J = 10.8 Hz, 1H), 2.33
1
3
H); C NMR (100 MHz, CDCl3): δ = 149.1, 133.4,
31.7, 130.9, 130.6, 129.8, 128.2, 127.5, 125.9, 116.2;
1
3
IR (film): ν = 3122, 3096, 2928, 2875, 1644, 1550,
(s, 3H); C NMR (100 MHz, CDCl3): δ = 148.4, 136.8,
132.9, 131.2, 130.1, 129.5, 125.9, 125.3, 121.7, 116.8,
20.9; IR (film): ν = 3114, 3086, 2926, 2874, 1642,
–1
1
495, 1441, 1225, 1001, 906, 817, 696 cm ; Calcd
for C10H8N3Cl: C 58.41, H 3.92, N 20.43; found:
C 58.31, H 4.02, N 20.32.
–1
1550, 1496, 1455, 1377, 1224, 995, 868, 695 cm ;
Calcd for C11H11N3: C 71.33, H 5.99, N 22.69; found:
C 71.22, H 6.11, N 22.80.
1
-(p-Bromophenyl)-4-vinyl-1H-1,2,3-triazole (5j).
1
Pale yellow solid, mp 140–141°C [39]; H NMR
(
8
1
(
400 MHz, CDCl3): δ = 7.84 (s, 1H), 7.68 (d, J =
4-(4-Vinyl-1,2,3-triazol-1-yl)phenol (5o). White
1
.8 Hz, 2H), 7.49 (d, J = 8.8 Hz, 2H), 6.80 (dd, J =
8.4, 11.2 Hz, 1H), 5.97 (d, J = 18.4 Hz, 1H), 5.49
solid, mp 83–85°C; H NMR (400 MHz, CDCl3): δ =
9.91 (s, 1H), 7.75 (s, 1H), 7.66 (d, J = 7.2 Hz, 2H),
6.96 (d, J = 7.2 Hz, 2H), 6.21 (dd, J = 17.6, 10.4 Hz,
1H), 6.00 (d, J = 17.6 Hz, 1H), 5.51 (d, J = 10.4 Hz,
1
3
d, J = 11.2 Hz, 1H); C NMR (100 MHz, CDCl3): δ =
1
48.8, 138.6, 134.1, 130.3, 129.6, 126.1, 120.2, 116.5.
1
3
1
H); C NMR (100 MHz, CDCl3): δ = 157.2, 148.8,
1
-(p-Nitrophenyl)-4-vinyl-1H-1,2,3-triazole (5k).
130.1, 129.3, 125.8, 122.2, 117.2, 114.8; IR (KBr):
1
Pale yellow solid, mp 177–178°C; H NMR (400 MHz,
ν = 3220, 3103, 1642, 1505, 1495, 1454, 1360, 1220,
Heteroatom Chemistry DOI 10.1002/hc