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(t, J ¼ 7.7 Hz, 2H), 7.28–7.21 (m, 3H), 6.86 (d, J ¼ 8.6 Hz, 2H),
5.44 (s, 2H), 3.76 (s, 3H); 13C NMR (100 MHz, CDCl3) d 159.8,
147.9, 130.5, 129.5 (2C), 128.6 (2C), 128.0, 126.6, 125.5 (2C),
119.3, 114.4 (2C), 55.2, 53.6; IR (neat, cmꢀ1) nmax 3107, 3083,
1483, 1461, 1219, 1073, 1010, 816, 799, 761, 687; HRMS (FAB):
calcd for C16H16N3O [M + H]+ 266.1293, found 266.1291.
1-Benzyl-4-(tert-butyl)-1H-1,2,3-triazole (4m)
White solid (105.1 mg, 98%); m.p. 84–86 ꢂC; 1H NMR (400 MHz,
CDCl3) d 7.29–7.24 (m, 3H), 7.19–7.17 (m, 2H), 7.15 (s, 1H), 5.39
(s, 2H), 1.25 (s, 9H); 13C NMR (100 MHz, CDCl3) d 157.8, 134.9,
128.7 (2C), 128.2, 127.7 (2C), 118.3, 53.6, 30.5, 30.1 (3C); IR
(neat, cmꢀ1) nmax 3119, 2961, 2865, 1531, 1495, 1457, 1361,
1341, 1231, 1202, 1051, 821, 713, 673; HRMS (FAB): calcd for
C
13H18N3 [M + H]+ 216.1501, found 216.1498.
Ethyl 1-benzyl-1H-1,2,3-triazole-4-carboxylate (4h)
White solid (113.3 mg, 98%); m.p. 84–86 ꢂC; 1H NMR (400 MHz,
CDCl3) d 7.98 (s, 1H), 7.25–7.17 (m, 5H), 5.48 (s, 2H), 4.25 (q, J ¼
7.2 Hz, 2H), 1.24 (t, J ¼ 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) d
160.3, 140.1, 133.7, 128.9 (2C), 128.6, 127.9 (2C), 127.2, 60.8,
54.0, 13.9; IR (neat, cmꢀ1) nmax 3126, 2983, 1715, 1539, 1368,
1226, 1044, 1022, 776, 716, 693; HRMS (FAB): calcd for
1-Benzyl-4-hexyl-1H-1,2,3-triazole (4n)
White solid (119.0 mg, 98%); m.p. 52–54 ꢂC; 1H NMR (400 MHz,
CDCl3) d 7.35–7.29 (m, 3H), 7.23–7.21 (m, 2H), 7.15 (s, 1H), 5.45
(s, 2H), 2.65 (t, J ¼ 7.8 Hz, 2H), 1.64–1.56 (m, 2H), 1.34–1.25 (m,
6H), 0.83 (t, J ¼ 6.7 Hz, 3H); 13C NMR (100 MHz, CDCl3) d 148.6,
134.9, 128.8 (2C), 128.3, 127.7 (2C), 120.4, 53.6, 31.3, 29.1, 28.7,
25.5, 22.3, 13.8; IR (neat, cmꢀ1) nmax 3112, 3065, 2957, 2919,
2853, 1553, 1493, 1456, 1433, 1325, 1212, 1130, 1051, 1029, 856,
703, 691; HRMS (FAB): calcd for C15H22N3 [M + H]+ 244.1814,
found 244.1816.
C
12H14N3O2 [M + H]+ 232.1086, found 232.1088.
1-Benzyl-4-(4-methoxyphenyl)-1H-1,2,3-triazole (4i)
White solid (132.3 mg, 100%); m.p. 142–144 ꢂC; 1H NMR
(400 MHz, CDCl3) d 7.71–7.69 (m, 2H), 7.56 (s, 1H), 7.37–7.27
(m, 5H), 6.92–6.89 (m, 2H), 5.52 (s, 2H), 3.80 (s, 3H); 13C NMR
(100 MHz, CDCl3) d 159.5, 147.9, 134.7, 129.0 (2C), 128.6, 127.9
(2C), 126.9 (2C), 123.2, 118.7, 114.1 (2C), 55.2, 54.0; IR (neat,
cmꢀ1) nmax 3138, 3040, 2949, 2838, 2098, 1614, 1557, 1495, 1454,
1436, 1349, 1249, 1170, 1070, 1027, 973, 832, 794, 717; HRMS
(FAB): calcd for C16H16N3O [M + H]+ 266.1293, found 266.1286.
1-Benzyl-4-cyclohexyl-1H-1,2,3-triazole (4o)
White solid (120.4 mg, 100%); m.p. 109–111 ꢂC; 1H NMR
(400 MHz, CDCl3) d 7.37–7.31 (m, 3H), 7.24–7.22 (m, 2H), 7.12
(s, 1H), 5.46 (s, 2H), 2.72–2.71 (m, 1H), 2.01–1.99 (m, 2H), 1.77–
1.66 (m, 3H), 1.37–1.29 (m, 4H), 1.22–1.18 (m, 1H); 13C NMR
(100 MHz, CDCl3) d 153.9, 134.9, 128.8 (2C), 128.3, 127.8 (2C),
119.1, 53.7, 35.1, 32.8 (2C), 25.9 (2C), 25.8; IR (neat, cmꢀ1) nmax
3121, 2925, 2851, 1540, 1495, 1450, 1264, 1208, 1128, 1049, 821,
754, 721, 699; HRMS (FAB): calcd for C15H20N3 [M + H]+
242.1657, found 242.1660.
tert-Butyl((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)carbamate
(4j)
Light yellow solid (137.0 mg, 95%); m.p. 91–93 ꢂC; 1H NMR
(400 MHz, CDCl3) d 7.40 (s, 1H), 7.37–7.23 (m, 5H), 5.48 (s, 2H),
5.04 (brs, 1H, NH), 4.34 (d, J ¼ 5.9 Hz, 2H), 1.39 (s, 9H); 13C NMR
(100 MHz, CDCl3) d 155.7, 145.7, 134.5, 128.9 (2C), 128.5, 127.8
(2C), 121.7, 79.3, 53.9, 35.9, 28.2 (3C); IR (neat, cmꢀ1) nmax 3405,
3111, 3063, 2978, 2954, 1688, 1515, 1454, 1268, 1169, 1123,
1054, 796, 717, 695; HRMS (FAB): calcd for C15H21N4O2 [M + H]+
289.1665, found 289.1666.
1-Benzyl-1H-1,2,3-triazole-4-carboxylic acid (4p)
White solid (92.1 mg, 91%); m.p. 184–185 ꢂC; 1H NMR
(400 MHz, (CD3)2SO) d 12.92 (brs, 1H, CO2H) 8.75 (s, 1H), 7.40–
7.33 (m, 5H), 5.64 (s, 2H); 13C NMR (100 MHz, (CD3)2SO) d 161.6,
140.1, 135.6, 128.9, 128.8 (2C), 128.2, 128.0 (2C), 53.0; IR (neat,
cmꢀ1) nmax 3115, 2556, 1681, 1540, 1495, 1425, 1232, 1049, 944,
895, 783, 714, 687; HRMS (FAB): calcd for C10H10N3O2 [M + H]+
204.0773, found 204.0767.
(1-Benzyl-1H-1,2,3-triazol-4-yl)methanol (4k)
White solid (93.4 mg, 99%); m.p. 77–79 ꢂC; 1H NMR (400 MHz,
CDCl3) d 7.43 (s, 1H), 7.31–7.28 (m, 3H), 7.21–7.19 (m, 2H), 5.42
(s, 2H), 4.67 (s, 2H), 3.71 (brs, 1H, OH); 13C NMR (100 MHz,
CDCl3) d 148.2, 134.4, 129.0 (2C), 128.6, 128.0 (2C), 121.8, 55.9,
54.0; IR (neat, cmꢀ1) nmax 3252, 3140, 2934, 1457, 1222, 1129,
1036, 1012, 837, 788, 717, 691; HRMS (FAB): calcd for
(1-Benzyl-1H-1,2,3-triazol-4-yl)methanamine (4q)
White solid (91.2 mg, 97%); m.p. 106–109 ꢂC; 1H NMR
(400 MHz, (CD3)2SO) d 7.92 (s, 1H), 7.39–7.30 (m, 5H), 5.56 (s,
2H), 3.75 (s, 2H), 2.31 (brs, 2H, NH2); 13C NMR (100 MHz,
(CD3)2SO) d 150.1, 136.2, 128.7 (2C), 128.0, 127.9 (2C), 121.8,
52.7, 37.2; IR (neat, cmꢀ1) nmax 3345, 3137, 2917, 1604, 1494,
1454, 1328, 1212, 1124, 1050, 898, 802, 726, 693, 668; HRMS
(FAB): calcd for C10H13N4 [M + H]+ 189.1140, found 189.1135.
C
10H12N3O [M + H]+ 190.0980, found 190.0980.
1-(1-Benzyl-1H-1,2,3-triazol-4-yl)cyclohexan-1-ol (4l)
White solid (122.1 mg, 95%); m.p. 125–126 ꢂC; 1H NMR
(400 MHz, CDCl3) d 7.35 (s, 1H), 7.31–7.25 (3H), 7.19–7.17 (m,
2H), 5.40 (s, 2H), 3.05 (brs, 1H, OH), 1.91–1.25 (m, 10H); 13C
NMR (100 MHz, CDCl3) d 156.0, 134.6, 128.8 (2C), 128.4, 127.9
2-(4-Phenyl-1H-1,2,3-triazol-1-yl)ethan-1-amine (4r)
White solid (92.0 mg, 98%); m.p. 75–77 ꢂC; 1H NMR (400 MHz,
(2C), 119.5, 69.3, 53.8, 37.9 (2C), 25.2, 21.7 (2C); IR (neat, cmꢀ1
)
nmax 3293, 2933, 2856, 1497, 1454, 1334, 1250, 1217, 1158, 1055, (CD3)2SO) d 8.54 (s, 1H), 7.84 (d, J ¼ 7.3 Hz, 2H), 7.44 (t, J ¼ 7.5
979, 795, 727; HRMS (FAB): calcd for C15H20N3O [M + H]+ Hz, 2H), 7.32 (t, J ¼ 7.3 Hz, 1H), 4.36 (t, J ¼ 6.2 Hz, 2H), 3.02 (m,
258.1606, found 258.1599.
2H); 13C NMR (100 MHz, (CD3)2SO) d 146.1, 130.9, 128.8 (2C),
RSC Adv., 2014, 4, 26516–26523 | 26521
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