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PRACTICAL SYNTHETIC PROCEDURES
MS (EI, 70 eV): m/z (%) = 249 (11, [M+]), 220 (52), 206 (15), 179
(16), 130 (100), 115 (15), 103 (25), 91 (93), 77 (27), 65 (26).
1H NMR (250 MHz, CDCl3): d = 7.66–7.59 (m, 2 H), 7.49 (s, 1 H),
7.30–7.16 (m, 5 H), 6.86–6.81 (m, 2 H), 5.43 (s, 2 H), 3.71 (s, 3 H).
13C NMR (62.5 MHz, CDCl3): d = 159.5, 147.9, 134.7, 129.0,
1-Benzyl-4-m-tolyl-1H-1,2,3-triazole (3d)
Yield: 94 mg (76%, 0.38 mmol); white solid; mp 144–146 °C;
Rf = 0.44 (hexanes–EtOAc, 3:1).
1H NMR (250 MHz, CDCl3): d = 7.57 (br s, 1 H), 7.56 (s, 1 H),
7.51–7.45 (m, 1 H), 7.30–7.16 (m, 6 H), 7.07–7.01 (m, 1 H), 5.47
(s, 2 H), 2.28 (s, 3 H).
128.6, 127.9, 126.9, 123.2, 118.7, 114.1, 55.2, 54.0.
MS (EI, 70 eV): m/z (%) = 265 (18, [M+]), 236 (92), 222 (18), 209
(20), 193 (13), 179 (18), 160 (12), 146 (88), 119 (38), 103 (15), 91
(100), 76 (29), 65 (37).
1-Benzyl-4-(4-nitrophenyl)-1H-1,2,3-triazole (3i)
Yield: 45 mg (32%, 0.16 mmol); yellow solid; mp 167–169 °C;
Rf = 0.26 (hexanes–EtOAc, 3:1).
13C NMR (62.5 MHz, CDCl3): d = 148.3, 138.4, 134.7, 130.3,
129.1, 128.9, 128.7, 128.6, 128.0, 126.3, 122.7, 119.4, 54.1, 21.3.
MS (EI, 70 eV): m/z (%) = 249 (11, [M+]), 220 (40), 206 (9), 179
(11), 130 (100), 115 (12), 103 (18), 91 (94), 77 (26), 65 (24).
1H NMR (250 MHz, CDCl3): d = 8.28–8.23 (m, 2 H), 7.99–7.94 (m,
2 H), 7.81 (s, 1 H), 7.42–7.31 (m, 5 H), 5.61 (s, 2 H).
13C NMR (62.5 MHz, CDCl3): d = 147.3, 146.0, 136.8, 134.1,
1-Benzyl-4-(2-isopropylphenyl)-1H-1,2,3-triazole (3e)
Yield: 90 mg (65%, 0.32 mmol); white solid; mp 74–75 °C;
Rf = 0.55 (hexanes–EtOAc, 3:1).
129.3, 129.0, 128.2, 126.1, 124.2, 120.9, 54.4.
MS (EI, 70 eV): m/z (%) = 280 (8, [M+]), 251 (23), 205 (12), 178
(9), 161 (35), 115 (18), 104 (18), 91 (100), 65 (23).
IR (ATR): 3134, 3064, 3031, 2962, 2867, 1497, 1482, 1456, 1344,
1210, 1030 cm–1.
1H NMR (250 MHz, CDCl3): d = 7.52 (s, 1 H), 7.46–7.30 (m, 8 H),
7.24–7.17 (m, 1 H), 5.60 (s, 2 H), 3.38 (sept, J = 6.9 Hz, 1 H), 1.22
(d, J = 6.9 Hz, 6 H).
13C NMR (62.5 MHz, CDCl3): d = 147.6, 147.0, 134.7, 129.9,
129.0, 128.9, 128.6, 128.6, 127.9, 125.6, 125.5, 121.8, 54.0, 29.2,
23.9.
MS (EI, 70 eV): m/z (%) = 277 (9, [M+]), 234 (5), 206 (12), 158
(18), 143 (11), 131 (15), 115 (24), 104 (3), 91 (100), 77 (6), 65 (15),
51 (4).
3-(1-Benzyl-1H-1,2,3-triazol-4-yl)benzonitrile (3j)
Yield: 81 mg (62%, 0.31 mmol); white solid; mp 109–110 °C;
Rf = 0.23 (hexanes–EtOAc, 3:1).
IR (ATR): 3122, 2923, 2226, 1670, 1607, 1450, 1228, 1048 cm–1.
1H NMR (250 MHz, CDCl3): d = 8.04–8.00 (m, 2 H), 7.79 (s, 1 H),
7.61–7.28 (m, 7 H), 5.57 (s, 2 H).
13C NMR (62.5 MHz, CDCl3): d = 145.8, 134.2, 131.8, 131.2,
129.6, 129.5, 129.1, 128.9, 128.8, 128.0, 120.2, 118.4, 112.8, 54.2.
MS (EI, 70 eV): m/z (%) = 260 (7, [M+]), 231 (34), 204 (12), 141
(70), 114 (26), 104 (18), 91 (100), 77 (8), 65 (27).
HRMS: m/z [M + H]+ calcd for C18H20N3: 278.1652; found:
278.1655.
HRMS: m/z [M + H]+ calcd for C16H13N4: 261.1135; found:
261.1140.
1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole (3f)
Yield: 78 mg (0.27 mmol, 55%); white solid; mp 74–75 °C;
Rf = 0.36 (hexanes–EtOAc, 3:1).
1-Benzyl-4-(4-bromophenyl)-1H-1,2,3-triazole (3k)
Yield: 94 mg (60%, 0.30 mmol); white solid; mp 147–148 °C;
Rf = 0.42 (hexanes–EtOAc, 3:1).
1H NMR (250 MHz, CDCl3): d = 7.68–7.63 (m, 3 H), 7.53–7.47 (m,
2 H), 7.41–7.35 (m, 3 H), 7.32–7.28 (m, 2 H), 5.55 (s, 2 H).
13C NMR (62.5 MHz, CDCl3): d = 147.1, 134.4, 131.9, 129.4,
129.1, 128.8, 128.0, 127.1, 121.9, 119.5, 54.2.
IR (ATR): 3132, 3050, 2930, 1592, 1497, 1455, 1348, 1218, 1049
cm–1.
1H NMR (250 MHz, CDCl3): d = 8.25–8.18 (m, 1 H), 7.71–7.65 (m,
2 H), 7.53 (s, 1 H), 7.51–7.47 (m, 1 H), 7.34–7.27 (m, 3 H), 7.21–
7.13 (m, 5 H), 5.42 (s, 2 H).
MS (EI, 70 eV): m/z (%) = 315 (5, [M+]), 286 (17), 206 (18), 194
(40), 179 (20), 167 (10), 115 (13), 104 (14), 91 (100), 75 (8), 65
(26).
13C NMR (62.5 MHz, CDCl3): d = 147.2, 134.6, 133.7, 130.9,
129.0, 128.7, 128.6, 128.3, 128.0, 127.9, 127.1, 126.5, 125.8, 125.3,
125.2, 122.4, 54.1.
MS (EI, 70 eV): m/z (%) = 285 (15, [M+]), 256 (84), 229 (16), 180
(8), 166 (85), 152 (22), 139 (65), 91 (100), 77 (6), 65 (25).
HRMS: m/z [M + H]+ calcd for C19H16N3: 286.1339; found:
1-Benzyl-4-(thiophen-2-yl)-1H-1,2,3-triazole (3l)
Yield: 65 mg (54%, 0.27 mmol); white solid; mp 120–122 °C;
Rf = 0.37 (hexanes–EtOAc, 3:1).
286.1342.
1H NMR (250 MHz, CDCl3): d = 7.49 (s, 1 H), 7.29–7.14 (m, 7 H),
6.94–6.91 (m, 1 H), 5.42 (s, 2 H).
4-(1-Benzyl-1H-1,2,3-triazol-4-yl)benzenamine (3g)
Yield: 87 mg (0.35 mmol, 70%); white solid; mp 182–185 °C
(dec.); Rf = 0.34 (hexanes–EtOAc, 1:1).
1H NMR (250 MHz, CDCl3): d = 7.62–7.56 (m, 2 H), 7.52 (s, 1 H),
7.41–7.27 (m, 5 H), 6.73–6.68 (m, 2 H), 5.55 (s, 2 H), 3.74 (br s, 2
H).
13C NMR (62.5 MHz, CDCl3): d = 146.5, 134.9, 129.1, 128.7,
128.0, 126.9, 126.1, 121.1, 118.1, 115.2, 54.1.
MS (EI, 70 eV): m/z (%) = 250 (22, [M+]), 221 (100), 194 (50), 145
(25), 131 (60), 117 (14), 104 (47), 91 (55), 77 (29), 65 (23).
13C NMR (62.5 MHz, CDCl3): d = 143.1, 134.4, 132.8, 129.0,
128.7, 127.9, 127.5, 124.9, 124.0, 119.0, 54.1.
MS (EI, 70 eV): m/z (%) = 241 (18, [M+]), 212 (100), 185 (34), 122
(50), 95 (20), 91 (89), 69 (26), 65 (32).
3-(1-Benzyl-1H-1,2,3-triazol-4-yl)pyridine (3m)
Yield: 75 mg (63%, 0.32 mmol); white solid; mp 100–102 °C;
Rf = 0.42 (EtOAc).
1H NMR (250 MHz, CDCl3): d = 8.93 (s, 1 H), 8.50 (d, J = 4.7 Hz,
1 H), 8.11 (d, J = 7.9 Hz, 1 H), 7.77 (s, 1 H), 7.35–7.28 (m, 6 H),
5.55 (s, 2 H).
1-Benzyl-4-(4-methoxyphenyl)-1H-1,2,3-triazole (3h)
Yield: 75 mg (57%, 0.285 mmol); white solid; mp 144–146 °C;
Rf = 0.26 (hexanes–EtOAc, 3:1).
13C NMR (62.5 MHz, CDCl3): d = 149.0, 146.8, 144.9, 134.3,
132.8, 129.0, 128.7, 127.9, 126.5, 123.5, 119.9, 54.2.
Synthesis 2009, No. 20, 3527–3532 © Thieme Stuttgart · New York