s, triazole-H); 13C NMR (100.5 MHz, d6-DMSO): d = 52.7 (1C,
CH2), 55.5 (1C, OMe), 111.5, 119.0, 120.6, 124.1, 126.5, 127.8,
128.1, 128.8, 129.0, 136.3, 142.0, 155.3 (14C, Ar); HR-ESIMS:
m/z = 266.12872 [M+H]+, calcd. 266.12879 for C16H16N3O.
4-Ethyl-1-((naphthalen-6-yl)methyl)-1H-1,2,3-triazole 14
◦
1
White solid, mp 73.5–76 C. H NMR (500 MHz, CDCl3): d =
1.23 (3H, t, J 7.5 Hz, (CH2)7CH3), 2.72 (2H, q, CH2CH3), 5.62
(2H, s, CH2N), 7.21 (1H, s, triazole-H), 7.34 (1H, dd, J 1.5, 8.5 Hz,
H7), 7.48–7.51 (2H, m, Ar), 7.18 (1H, d, J 1.5 Hz, H5), 7.80–7.83
(3H, m, Ar); 13C NMR (100.5 MHz, CDCl3): d = 13.5, 19.0 (2C,
CH2CH3), 54.1 (1C, CH2N), 120.1, 125.3, 126.5, 126.6, 127.2,
127.7, 127.8, 129.0, 132.3, 133.0, 133.1, 150.2 (12C, Ar); HR-
ESIMS: m/z = 238.13385 [M+H]+, calcd. 238.13387 for C15H16N3.
2-(4-Butyl-1H-1,2,3-triazol-1-yl)-N-phenylacetamide 9
White crystals from DMSO/H2O, mp 167.5–169.5 ◦C. 1H NMR
(500 MHz, d6-DMSO): d = 0.81 (3H, t, J 7.5 Hz, CH3), 1.23 (2H,
m, CH2), 1.51 (2H, m, CH2), 2.58 (2H, t, J 7.5 Hz, CH2), 5.18
(2H, s, CH2CO), 7.07 (1H, t, J 7.5 Hz, Ar–H), 7.29 (2H, t, J 7.5
Hz, Ar–H), 7.44 (2H, d, J 8.5 Hz, Ar–H), 7.76 (1H, s, triazole-H),
10.41 (1H, s, NH); 13C NMR (100.5 MHz, d6-DMSO): d = 14.1,
22.1, 25.6, 31.6, 52.5 (5C, 4 ¥ CH2, 1 ¥ CH3), 119.6, 123.9, 124.2,
129.3, 138.8, 147.1 (8C, Ar), 164.8 (1C, C O); HR-ESIMS: m/z =
259.15527 [M+H]+, calcd. 259.15534 for C14H19N4O.
1-(4-Methoxybenzyl)-4-ethyl-1H-1,2,3-triazole 15
White solid, mp 65.1–66.3 ◦C. 1H NMR (500 MHz, CDCl3): d =
1.23 (3H, t, J 7.5 Hz, CH2CH3), 2.72 (2H, q, CH2CH3), 3.80
(3H, s, OMe), 5.41 (2H, s, CH2N), 6.88 (2H, d, J 9.0 Hz, Ar),
7.15 (1H, s, triazole-H), 7.21 (2H, d, J 9.0 Hz, Ar); 13C NMR
(100.5 MHz, CDCl3): d = 13.6, 19.0 (2C, CH2CH3), 53.6, 55.3
(2C, CH2N, OMe), 114.4, 119.8, 126.9, 129.6, 148.8, 159.8 (8C,
Ar); HR-ESIMS: m/z = 218.12877 [M+H]+, calcd. 218.12879 for
C12H16N3O.
2-(4-Ethyl-1H-1,2,3-triazol-1-yl)-N-phenylacetamide 10
White crystals, mp 158–160 ◦C. 1H NMR (500 MHz, d6-DMSO):
d = 1.21 (3H, t, J 7.5 Hz, CH3), 2.65 (2H, q, J 7.5 Hz, CH2CH3),
5.26 (2H, s, CH2CO), 7.08 (1H, t, J 7.5 Hz, Ar), 7.33 (2H, t, J
7.5 Hz, Ar), 7.58 (2H, d, J 7.5 Hz, Ar), 7.86 (1H, s, triazole-H),
10.4 (1H, s, NH); 13C NMR (100.5 MHz, d6-DMSO): d = 13.7
(CH3), 18.4, 52.1 (CH2), 119.2, 123.0, 123.7, 128.9, 138.4, 148.1
(Ar), 164.3 (C O); HR-ESIMS: m/z = 231.12399 [M+H]+, calcd.
231.12404 for C12H15N4O.
1,4-bis((4-Phenyl-1H-1,2,3-triazol-1-yl)methyl)benzene 16
White crystals from EtOAc/pet. spirit, mp 207–209 ◦C. 1H NMR
(400 MHz, d6-DMSO): d = 5.64 (2H, s, CH2), 7.37 (4H, s, C6H4),
7.34–7.30 (2H, m, Ph), 7.44–7.41 (4H, m, Ph), 7.84–7.81 (4H, m,
Ph), 8.62 (2H, s, triazole-H); 13C NMR (100 MHz, d6-DMSO):
d = 52.5 (CH2), 99.7, 121.3, 125.0, 127.7, 128.2, 128.6, 130.5,
135.8, 146.5 (Ar); HR-ESIMS: m/z = 393.18207 [M+H]+, calcd.
393.18222 for C24H21N6.
4-Phenyl-1-octyl-1H-1,2,3-triazole 11
White crystals, mp 76–78 ◦C (lit.38 74–75 ◦C). 1H NMR (500 MHz,
d6-DMSO): d = 0.83 (3H, t, J 7 Hz, CH3), 1.22–1.28 (10H, m, 5 ¥
CH2), 1.84 (2H, t, J 7 Hz, CH2CH2N), 4.37 (2H, t, J 7 Hz, CH2–
N), 7.31 (1H, t, J 8 Hz, Ar), 7.43 (2H, t, J 8 Hz, Ar), 7.83 (2H,
d, J 8.5 Hz, Ar), 8.57 (1H, s, triazole-H); 13C NMR (100.5 MHz,
d6-DMSO): d = 13.9 (CH3), 22.0, 25.8, 28.3, 28.5, 29.6, 31.1, 49.5
(8C, 8 ¥ CH2), 121.2, 125.1, 127.7, 128.8, 130.9, 146.2 (8 C, Ar).
1,4-bis((4-Butyl-1H-1,2,3-triazol-1-yl)methyl)benzene 17
White crystals, mp 168–171 ◦C. 1H NMR (500 MHz, d6-DMSO):
d = 0.86 (6H, t, J 7.5 Hz, 2 ¥ CH3), 1.28 (4H, m, CH2CH2),
1.53 (4H, m, CH2CH3), 2.57 (4H, t, J 7.5 Hz, CH2C C), 5.51
(2H, s, CH2Ar), 7.19 (1H, s, triazole-H), 7.23 (4H, s, C6H4); 13C
NMR (100.5 MHz, d6-DMSO): d = 13.7, 21.7, 24.6, 31.1 (8C, 6 ¥
CH2, 2 ¥ CH3), 52.3 (2C, CH2Ph), 121.9, 128.2, 136.1, 147.3 (10C,
Ar); HR-ESIMS: m/z = 353.24484 [M+H]+, calcd. 353.24537 for
C20H29N6.
4-Ethyl-1-octyl-1H-1,2,3-triazole 12
◦
1
Yellow solid, mp 37.5–39 C. H NMR (500 MHz, CDCl3): d =
0.83 (3H, t, J 7.0 Hz, (CH2)7CH3), 1.19–1.26 (13H, m, 5 ¥ CH2,
1 ¥ CH3), 2.70 (2H, q, ArCH2CH3), 4.25 (2H, t, J 7.5 Hz, CH2N),
7.23 (1H, s, triazole-H); 13C NMR (100.5 MHz, CDCl3): d = 13.6,
13.9, 18.9, 22.5, 26.4, 28.3, 28.9, 30.2, 31.6, 50.1 (10C, 10 ¥ CH2),
119.9, 149.6 (2C, Ar); HR-ESIMS: m/z = 210.19646 [M+H]+,
calcd. 210.19647 for C12H24N3.
2-(4-Methyl-1H-1,2,3-triazol-1-yl)-N-phenylacetamide 18
White crystals from EtOAc/pet. spirit, m.p. 179–181 ◦C. 1H NMR
(500 MHz, d6-DMSO): d = 2.25 (3H, s, CH3), 5.26 (2H, s, CH2),
7.08 (1H, t, J 7.5 Hz, Ph), 7.33 (2H, t, J 7.5 Hz, Ph), 7.57 (2H, d, J
7.5 Hz, Ph), 7.84 (1H, s, triazole-H), 10.4 (1H, s, NH); 13C NMR
(125 MHz, d6-DMSO): d = 10.4 (CH3), 52.0 (CH2), 119.7, 123.7,
123.9, 128.9, 138.4, 141.7 (Ar), 164.3 (C O); HR-ESIMS: m/z =
239.09031 [M+Na]+, calcd. 239.09033 for C11H12N4NaO.
2-(4-(2-Methoxyphenyl)-1H-1,2,3-triazol-1-yl)-(N-(4-
biphenyl))acetamide 13
◦
1
Colourless crystals, mp 182–183 C. H NMR (500 MHz, d6-
DMSO): d = 3.91 (3H, s, CH3), 5.24 (2H, s, CH2), 7.04 (1H, t, J
8.0 Hz, Ar–H), 7.05 (1H, d, J 8.0 Hz, Ar–H), 7.31–7.38 (4H, m,
Ar–H), 7.39–7.47 (2H, m, Ar–H), 7.62–7.65 (4H, m, Ar–H), 8.16
(1H, dd, J 1.5, 7.5 Hz, Ar–H), 8.38 (1H, s, triazole-H); 13C NMR
(100.5 MHz, d6-DMSO): d = 42.1, 51.6, 55.5 (3C, 2 ¥ CH2, 1 ¥
CH3), 111.5, 119.1, 120.6, 125.5, 126.5, 126.6, 126.7, 127.4, 128.0,
128.8, 128.9, 138.0, 139.0, 139.9, 141.5, 155.3 (20C, Ar), 165.6 (1C,
1-(4-Methoxybenzyl)-4-butyl-1H-1,2,3-triazole 19
◦
1
White solid, mp 72–73.5 C. H NMR (500 MHz, CDCl3): d =
0.99 (3H, t, J 7.0 Hz, (CH2)3CH3), 1.30–1.38, 1.57–1.63 (2 ¥ 2H,
2 ¥ m, CH2CH2CH3), 2.66 (2H, t, J 8.0 Hz, CH2C C) 3.79 (3H,
s, OMe), 5.40 (2H, s, CH2N), 6.88 (2H, d, J 9.0 Hz, Ar), 7.14 (1H,
s, triazole-H), 7.20 (2H, d, J 9.0 Hz, Ar); 13C NMR (100.5 MHz,
CDCl3): d = 13.7, 22.2, 25.3, 31.4 (4C, (CH2)3CH3), 53.4, 55.2
C
O); HR-ESIMS: m/z = 399.18148 [M+H]+, calcd. 399.18155
for C24H23N4O2.
This journal is
The Royal Society of Chemistry 2011
Org. Biomol. Chem., 2011, 9, 6082–6088 | 6087
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