Vol. 30, No. 3, 2019
Teixeira et al.
549
0.750 mmol) and 8 (165 mg, 0.75 mmol). TLC: Rf = 0.31
5.59 (s, 2H), 7.28 (s, 1H), 7.35 (d, 2H, J 8.4 Hz), 8.18 (d,
2H, J 8.4 Hz); 13C NMR (75 MHz, CDCl3) d 17.6, 22.4,
23.5, 25.7, 26.7, 29.4, 32.2, 52.9, 67.0, 69.1, 121.0, 121.8,
123.8, 124.2, 128.4, 131.9, 140.3, 142.1, 147.9, 148.8; MS-
EI, m/z (%): 398 (0.2) C22H30N4O3 [M+•], 330 (0.3), 263 (8),
245 (12), 218 (22), 199 (5), 136 (10), 121 (4), 106 (19), 89
(15), 78 (34), 69 (58), 53 (18), 41 (100).
(hexane/ethyl acetate/dichloromethane 3:1:3 v/v); IR
(ATR)
/ cm-1 3132, 2962, 2928, 2856, 1667, 1620,
1446, 1325, 1218, 1166, 1127, 1067, 1018, 823; 1H NMR
(300 MHz, CDCl3) d 1.55 (s, 3H), 1.63 (s, 3H), 1.69 (s,
3H), 1.90 (quint, 2H, J 6.3 Hz), 2.02 (s, 4H), 2.76 (t, 2H,
J 6.3 Hz), 3.41 (t, 2H, J 6.3 Hz), 3.90 (d, 2H, J 6.9 Hz),
5.05 (brs, 1H), 5.29 (t, 1H, J 6.9 Hz), 5.52 (s, 2H), 7.24
(s, 1H), 7.31 (d, 2H, J 8.4 Hz), 7.58 (d, 2H, J 8.4 Hz);
13C NMR (75 MHz, CDCl3) d 17.6, 22.3, 23.4, 25.6, 26.6,
29.3, 32.2, 53.2, 67.0, 69.1, 120.9, 121.8, 123.8, 124.8 (q,
JC-F 270.0 Hz), 126.0 (q, JC-F 3.6 Hz), 128.0, 130.8 (q, JC-F
32.4 Hz), 131.8, 139.0, 140.2, 148.5; MS-EI, m/z (%): 421
(0.2) C23H30F3N3O [M+•], 353 (2), 286 (40), 268 (44), 241
(77), 212 (3), 159 (100), 140 (5), 121 (11), 109 (33), 93
(30), 80 (17), 69 (62), 53 (21), 41 (96).
(Z)-1-(3,4-Difluorobenzyl)-4-(3-((3,7-dimethylocta-2,6-dien-
1-yl)oxy)propyl)-1H-1,2,3-triazole (10j)
Compound 10j was obtained as a yellow oil in 96%
yield (276 mg, 0.710 mmol) from compounds 3j (126.8 mg,
0.750 mmol) and 8 (165 mg, 0.750 mmol). 5 mg of
unreacted compound 8 was also recovered. TLC: Rf = 0.35
(hexane/ethyl acetate/dichloromethane 3:1:3 v/v); IR (ATR)
/ cm-1 3133, 2960, 2926, 2856, 1715, 1668, 1611,
1519, 1439, 1376, 1286, 1214, 1115, 1047, 782, 574, 524,
452; 1H NMR (300 MHz, CDCl3) d 1.56 (s, 3H), 1.63 (s,
3H), 1.70 (s, 3H), 1.91 (quint, 2H, J 6.3 Hz), 2.03 (s, 4H),
2.76 (t, 2H, J 6.3 Hz), 3.41 (t, 2H, J 6.3 Hz), 3.90 (d, 2H,
J 6.9 Hz), 5.05 (brs, 1H), 5.30 (t, 1H, J 6.9 Hz), 5.42 (s,
2H), 6.99-7.17 (m, 3H), 7.23 (s, 1H); 13C NMR (75 MHz,
CDCl3) d 17.6, 22.3, 23.4, 25.6, 26.6, 29.3, 32.2, 52.8,
67.0, 69.1, 116.9-117.1 (m), 117.7-118.0 (m), 120.8, 121.8,
123.8, 123.9-124.0 (m), 131.9, 140.2, 148.5, 148.6-148.9
(m), 151.9-152.0 (m), 152.1-152.2 (m); MS-EI, m/z (%):
389 (0.20) C22H29F2N3O [M+•], 321 (3), 262 (5), 254 (50),
236 (39), 209 (74), 180 (3), 127 (100), 93 (36), 80 (20), 69
(58), 53 (22), 41 (80).
(Z)-4-(3-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)propyl)-
1-(4-methoxybenzyl)-1H-1,2,3-triazole (10h)
Compound 10h was obtained as a yellow oil in 76%
yield (186 mg, 0.480 mmol) from compounds 3h (122 mg,
0.750 mmol) and 8 (165 mg, 0.750 mmol). 25 mg of
unreacted compound 8 was also recovered. TLC: Rf = 0.34
(hexane/ethyl acetate/dichloromethane 3:1:3 v/v); IR (ATR)
/ cm-1 3131, 3072, 2959, 2929, 2854, 1714, 1667, 1550,
1514, 1445, 1375, 1249, 1178, 1102, 1034, 823, 783, 514;
1H NMR (300 MHz, CDCl3) d 1.56 (s, 3H), 1.63 (s, 3H),
1.70 (s, 3H), 1.88 (quint, 2H, J 6.3 Hz), 2.03 (s, 4H), 2.72
(t, 2H, J 6.3 Hz), 3.40 (t, 2H, J 6.3 Hz), 3.76 (s, 3H), 3.89
(d, 2H, J 6.9 Hz), 5.05 (brs, 1H), 5.29 (t, 1H, J 6.9 Hz),
5.38 (s, 2H), 6.84 (d, 2H, J 8.4 Hz), 7.15 (s, 1H), 7.18 (d,
J 8.4 Hz); 13C NMR (75 MHz, CDCl3) d 17.5, 22.2, 23.3,
25.6, 26.6, 29.3, 32.1, 53.4, 55.2, 66.9, 69.1, 114.3, 120.4,
121.8, 123.7, 126.8, 129.4, 131.8, 140.1, 147.9, 159.7;
MS-EI, m/z (%): 383 (0.3) C23H33N3O2 [M+•], 315 (4), 262
(2), 248 (13), 231 (5), 203 (20), 121 (100), 110 (16), 93
(15), 77 (18), 69 (27), 53 (11), 41 (58).
(Z)-1-(2,5-Dichlorobenzyl)-4-(3-((3,7-dimethylocta-2,6-dien-
1-yl)oxy)propyl)-1H-1,2,3-triazole (10k)
Compound 10k was obtained as a yellow oil in 70%
yield (174 mg, 0.410 mmol) from compounds 3k (152 mg,
0.750 mmol) and 8 (165 mg, 0.750 mmol). 35 mg of
unreacted compound 8 was also recovered. TLC: Rf = 0.51
(hexane/ethyl acetate/dichloromethane 3:1:3 v/v); IR
(ATR)
/ cm-1 3134, 3071, 2959, 2926, 2855, 1722,
(Z)-4-(3-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)propyl)-
1-(4-nitrobenzyl)-1H-1,2,3-triazole (10i)
1667, 1552, 1464, 1376, 1272, 1219, 1099, 1045, 815,
522; H NMR (300 MHz, CDCl3) d 1.57 (s, 3H), 1.65
1
Compound 10i was obtained as a yellow oil in 71%
yield (200 mg, 0.500 mmol) from compounds 3i (134 mg,
0.750 mmol) and 8 (165 mg, 0.750 mmol). 20 mg of
unreacted compound 8 was also recovered. Yellow oil,
TLC: Rf = 0.26 (hexane/ethyl acetate/dichloromethane
(s, 3H), 1.71 (s, 3H), 1.93 (quint, 2H, J 6.3 Hz), 2.04 (s,
4H), 2.79 (t, 2H, J 6.3 Hz), 3.43 (t, 2H, J 6.3 Hz), 3.92 (d,
2H, J 6.9 Hz), 5.08 (brs, 1H), 5.32 (t, 1H, J 6.9 Hz), 5.56
(s, 2H), 7.06 (d, 1H, J 2.1 Hz), 7.24 (dd, 1H, J1 8.4 and
J2 2.1 Hz), 7.32 (s, 1H), 7.34 (d, 1H, J 8.4 Hz); 13C NMR
(75 MHz, CDCl3) d 17.6, 22.4, 23.5, 25.7, 26.7, 29.4, 32.2,
50.7, 67.0, 69.1, 121.2, 121.9, 123.8, 129.8, 130.0, 130.9,
131.3, 131.9, 133.5, 134.4, 140.2, 148.3; MS-EI, m/z (%):
422 (0.1) C22H29Cl2N3O [M+•], 353 (1), 286 (11), 268 (13),
241 (38), 204 (4), 159 (47), 123 (13), 93 (15), 69 (58), 53
(15), 41 (100).
3:1:3 v/v); IR (ATR)
/ cm-1 3133, 3078, 2961, 2926,
2855, 1668, 1606, 1522, 1446, 1346, 1218, 1105, 1046,
858, 804, 734; 1H NMR (300 MHz, CDCl3) d 1.56 (s, 3H),
1.64 (s, 3H), 1.71 (s, 3H), 1.92 (quint, 2H, J 6.3 Hz), 2.03
(s, 4H), 2.78 (t, 2H, J 6.3 Hz), 3.43 (t, 2H, J 6.3 Hz), 3.91
(d, 2H, J 6.9 Hz), 5.05 (brs, 1H), 5.30 (t, 1H, J 6.9 Hz),