Med Chem Res
1-(2-((2-chlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-
1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)
1H-1,2,4-triazole (5b)
ethyl)-1H-1,2,4-triazole (5e)
Yield: 40.7 %; light yellow solid; IR (KBr) (ν/cm–1) 3128,
3067 (Ar–H), 2959, 2919, 2869 (CH2), 1582, 1512
(Ar–C=C), 1470 (CH2), 1099 (Ar–Cl), 1045, 1020
(C–O–C); 1H NMR (600 MHz, CDCl3) δ ppm: 8.12 (d, J =
12.0 Hz, 1H, triazole–H5), 7.90 (s, 1H, triazole–H3),
7.47–7.42 (m, 2H, Ar–H), 7.33–7.30 (m, 2H, Ar–H),
7.24–7.21 (m, 2H, Ar–H), 7.20–7.17 (m, 1H, Ar–H), 5.21
(dt, J = 14.9, 7.4 Hz, 1H, CH), 4.55–4.44 (m, 2H, OCH2),
4.36–4.25 (m, 2H, CH2); 13C NMR (151 MHz, CDCl3) δ
ppm: 151.8, 144.3 (triazole–C3 and C5), 135.1, 134.4,
133.8, 133.7, 133.4, 129.8, 129.6, 129.5, 129.4, 128.5,
127.9, 126.9 (Ar–C), 76.1 (CH), 68.9 (OCH2), 53.9 (CH2);
HRMS m/z (pos): 382.0236 C17H14Cl3N3O [M + H]+
(Calcd, 382.0281).
Yield: 39.7 %; light yellow solid; IR (KBr) (ν/cm–1) 3101
(Ar–H), 2943, 2919 (CH2), 1589, 1563, 1555, 1505
(Ar–C=C), 1470, 1448 (CH2), 1096 (Ar–Cl), 1038, 1016
(C–O–C); 1H NMR (600 MHz, CDCl3) δ ppm: 8.11 (s, 1H,
triazole–H5), 7.92 (s, 1H, triazole–H3), 7.47–7.40 (m, 2H,
Ar–H), 7.35–7.31 (m, 2H, Ar–H), 7.21 (dd, J = 8.2, 2.0 Hz,
1H, Ar–H), 7.10 (d, J = 8.2 Hz, 1H, Ar–H), 5.21 (dd, J =
8.5, 2.9 Hz, 1H, CH), 4.50–4.43 (m, 2H, OCH2), 4.31–4.25
(m, 2H, CH2); 13C NMR (151 MHz, CDCl3) δ ppm: 151.9,
144.2 (triazole–C3 and C5), 135.2, 134.6, 134.0, 133.7,
133.6, 133.0, 130.3, 129.9, 129.3, 128.4, 128.0, 127.3
(Ar–C), 76.2 (CH), 68.3 (OCH2), 53.8 (CH2); HRMS m/z
(pos): 415.9838 C17H13Cl4N3O [M + H]+ (Calcd,
415.9891).
1-(2-((3-chlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-
1H-1,2,4-triazole (5c)
1-(2-(2,4-dichlorophenyl)-2-((2-fluorobenzyl)oxy)ethyl)-
1H-1,2,4-triazole (5f)
Yield: 74.6 %; light yellow solid; IR (KBr) (ν/cm–1) 3132,
3078 (Ar–H), 2947, 2919, 2881 (CH2), 1585, 1560, 1504
(Ar–C=C), 1466 (CH2), 1092 (Ar–Cl), 1042, 1018
(C–O–C); 1H NMR (600 MHz, CDCl3) δ ppm: 8.11 (d, J =
17.1 Hz, 1H, triazole–H5), 7.94 (s, 1H, triazole–H3),
7.47–7.38 (m, 2H, Ar–H), 7.35–7.31 (m, 1H, Ar–H),
7.26–7.18 (m, 2H, Ar–H), 7.06 (d, J = 11.9 Hz, 1H, Ar–H),
6.94 (d, J = 7.4 Hz, 1H, Ar–H), 5.16 (dd, J = 8.5, 3.0 Hz,
1H, CH), 4.47–4.40 (m, 2H, OCH2), 4.25 (ddd, J = 55.7,
22.5, 8.7 Hz, 2H, CH2); 13C NMR (151 MHz, CDCl3) δ
ppm: 152.0, 144.2 (triazole–C3 and C5), 138.7, 135.2, 134.4,
133.8, 133.7, 129.8, 128.5, 128.3, 128.0, 127.7, 125.7
(Ar–C), 75.7 (CH), 70.8 (OCH2), 53.2 (CH2); HRMS m/z
(pos): 382.0292 C17H14Cl3N3O [M + H]+ (Calcd, 382.0281).
Yield: 95.3 %; light yellow solid; IR (KBr) (ν/cm–1) 3130,
3088, 3063 (Ar–H), 2953, 2924, 2856 (CH2), 1584, 1560,
1508 (Ar–C=C), 1458 (CH2), 1236 (Ar–F), 1090 (Ar–Cl),
1
1045, 1018 (C–O–C); H NMR (500 MHz, CDCl3) δ ppm:
8.12 (s, 1H, triazole–H5), 7.90 (s, 1H, triazole–H5),
7.46–7.42 (m, 2H, Ar–H), 7.30 (ddd, J = 9.7, 5.4, 1.9 Hz,
2H, Ar–H), 7.11 (dtd, J = 15.3, 7.7, 1.1 Hz, 2H, Ar–H),
7.04–6.98 (m, 1H, Ar–H), 5.18 (dd, J = 8.5, 2.8 Hz, 1H,
CH), 4.52 (d, J = 11.6 Hz, 1H, OCH2), 4.45 (dd, J = 14.3,
2.9 Hz, 1H, OCH2), 4.31–4.22 (m, 2H, CH2); 13C NMR
(151 MHz, CDCl3) δ ppm: 161.8 (2-fluorophenyl C2),
151.7, 144.2 (triazole–C3 and C5), 135.1, 133.8, 133.7,
130.3, 130.2, 129.7, 128.5, 127.9, 124.2, 124.2, 115.5
(Ar–C), 75.9 (CH), 65.5 (OCH2), 53.9 (CH2); HRMS m/z
(pos): 366.0571 C17H14Cl2FN3O [M + H]+ (Calcd,
366.0576).
1-(2-((4-chlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-
1H-1,2,4-triazole (5d)
1-(2-(2,4-dichlorophenyl)-2-((4-fluorobenzyl)oxy)ethyl)-
1H-1,2,4-triazole (5g)
Yield: 37.1 %; light yellow solid; IR (KBr) (ν/cm–1) 3132,
3075, 3046 (Ar–H), 2957, 2926, 2894 (CH2), 1585, 1559,
1501, 1489 (Ar–C=C), 1462 (CH2), 1096 (Ar–Cl), 1038,
Yield: 96.4 %; light yellow solid; IR (KBr) (ν/cm–1) 3129,
3078, 3040 (Ar–H), 2945, 2924, 2875 (CH2), 1585, 1560,
1508 (Ar–C=C), 1467 (CH2), 1223 (Ar–F), 1092 (Ar–Cl),
1043, 1015 (C–O–C);1H NMR (600 MHz, CDCl3) δ ppm:
8.12 (s, 1H, triazole–H5), 7.92 (s, 1H, triazole–H3),
7.47–7.40 (m, 2H, Ar–H), 7.33 (dd, J = 8.3, 1.9 Hz, 1H,
Ar–H), 7.04 (dd, J = 8.3, 5.6 Hz, 2H, Ar–H), 6.98 (t, J =
8.6 Hz, 2H, Ar–H), 5.14 (dd, J = 8.6, 2.9 Hz, 1H, CH),
4.45–4.39 (m, 2H, OCH2), 4.28–4.13 (m, 2H, CH2); 13C
NMR (151 MHz, CDCl3) δ ppm: 163.4 (2-fluorophenyl C2),
151.9, 144.2 (triazole–C3 and C5), 135.1, 133.8, 133.7,
132.4, 132.4, 129.7, 129.7, 128.5, 128.0, 115.5, 115.4
1
1016 (C–O–C); H NMR (600 MHz, CDCl3) δ ppm: 8.11
(d, J = 11.2 Hz, 1H, triazole–H5), 7.93 (s, 1H, triazole–H3),
7.43 (dt, J = 14.2, 3.9 Hz, 2H, Ar–H), 7.35–7.31 (m, 1H,
Ar–H), 7.27 (s, 1H, Ar–H), 7.26 (s, 1H, Ar–H), 7.00 (d, J =
8.3 Hz, 2H, Ar–H), 5.14 (dt, J = 17.8, 8.9 Hz, 1H, CH),
4.46–4.39 (m, 2H, OCH2), 4.28–4.14 (m, 2H, CH2); 13C
NMR (151 MHz, CDCl3) δ ppm: 151.9, 144.2 (triazole–C3
and C5), 135.1, 135.1, 134.0, 133.8, 133.7, 129.8, 129.1,
128.7, 128.5, 128.0 (Ar–C), 75.5 (CH), 70.8 (OCH2), 53.8
(CH2); HRMS m/z (pos): 382.0289 C17H14Cl3N3O [M +
H]+ (Calcd, 382.0281).