12 of 15
SOLTANI RAD ET AL.
143.98 (C(4) of triazole), 139.05 (C(5) of imidazole),
134.95 (ArC), 132.27 (C(4) of imidazole), 130.53 (ArC),
128.23 (ArC‐Cl), 127.59 (ArC‐Cl), 121.18 (C(5) of
triazole), 118.25 (ArC), 77.86 (OCH2), 70.20 (CHOH),
58.80 (NCH2CH), 41.22 (NCH2C=C), 6.99 (CH3). MS
(EI): m/z (%) = 426 (38.4) [M+]. Anal. Calc. for
C16H16Cl2N6O4: C, 44.98; H, 3.77; N, 19.67; found: C,
45.12; H, 3.90; N, 19.83.
128.05 (C(5) of triazole), 121.81 (ArC‐Cl), 120.10 (ArC),
116.14 (ArC), 78.05 (OCH2), 70.67 (CHOH), 58.46
(NCH2CH), 43.11 (NCH2C=C), 5.61 (CH3). MS (EI):
m/z (%)
=
392 (31.9) [M+]. Anal. Calc. for
C16H17ClN6O4: C, 48.92; H, 4.36; N, 21.40; found: C,
49.03; H, 4.47; N, 21.51.
4.7.6 | 1‐(4‐ethylphenoxy)‐3‐(4‐((2‐methyl‐
5‐nitro‐1H‐imidazol‐1‐yl)methyl)‐1H‐1,2,3‐
triazol‐1‐yl)propan‐2‐ol (14f)
4.7.4 | 1‐(2‐methoxyphenoxy)‐3‐(4‐((2‐
methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl)‐
1H‐1,2,3‐triazol‐1‐yl) propan‐2‐ol (14d)
Column Chromatography on silica gel eluted with EtOAc
afforded pure product as white solid (3.01 g, 78%); m.p.
115–116 °C. IR (KBr): 3290, 3100, 2957, 1552, 1490,
Column Chromatography on silica gel eluted with EtOAc
afforded pure product as white solid (3.53 g, 91%); m.p.
152–153 °C. IR (KBr): 3200, 3050, 2954, 1550, 1465,
1430, 1351, 1245, 1050 cm−1
.
1H NMR (CDCl3,
300 MHz) δppm = 7.77 (s, 1H, C(4)‐H of imidazole), 7.73
(s, 1H, C(5)‐H of triazole), 7.11 (d, J = 8.7 Hz, 2H, aryl),
6.80 (d, J = 8.4 Hz, 2H, aryl), 5.17 (s, 2H, NCH2), 4.74
(dd, J = 3.0, 14.1 Hz, 1H, OCHAHB), 4.55 (dd, J = 7.5,
14.1 Hz, 1H, OCHAHB), 4.40 (br s, 1H, OH), 4.00–3.88
(m, 2H, NCH2), 3.71–3.70 (m, 1H, CHOH), 2.61
(q, J = 7.5 Hz, 2H, CH2CH3), 2.45 (s, 3H, CH3), 1.21
(t, J = 7.5 Hz, 3H, CH2CH3). 13C NMR (CDCl3,
75 MHz) δppm = 163.28 (ArC‐O), 159.99 (C(2) of imidaz-
ole), 144.80 (C(4) of triazole), 139.11 (C(5) of imidazole),
135.69 (ArC‐Et), 132.58 (C(4) of imidazole), 132.02
(ArC), 128.86 (C(5) of triazole), 114.66 (ArC), 78.61
(OCH2), 70.09 (CHOH), 57.60 (NCH2CH), 43.39
(NCH2C=C), 29.18 (CH2CH3), 17.54 (CH2CH3), 6.76
(CH3). MS (EI): m/z (%) = 386 (18.2) [M+]. Anal. Calc.
for C18H22N6O4: C, 55.95; H, 5.74; N, 21.75; found: C,
56.10; H, 5.89; N, 21.86.
1425, 1351, 1248, 1045 cm−1
.
1H NMR (CDCl3,
300 MHz) δppm = 7.74 (s, 1H, C(4)‐H of imidazole), 7.72
(s, 1H, C(5)‐H of triazole), 7.25–7.17 (m, 2H, aryl), 6.91–
6.89 (m, 2H, aryl), 5.19 (s, 2H, NCH2), 4.72 (dd, J = 3.3,
13.8 Hz, 1H, OCHAHB), 4.57 (dd, J = 6.9, 14.1 Hz, 1H,
OCHAHB), 4.36 (br s, 1H, OH), 4.07–4.02 (m, 2H,
NCH2), 3.92–3.87 (m, 1H, CHOH), 3.84 (s, 3H, OCH3),
2.48 (s, 3H, CH3). 13C NMR (CDCl3, 75 MHz)
δppm = 162.97 (C(2) of imidazole), 148.22 (ArC‐OCH3),
145.20 (ArC‐OCH2), 144.30 (C(4) of triazole), 139.47
(C(5) of imidazole), 135.55 (C(4) of imidazole), 132.22
(C(5) of triazole), 123.19 (ArC), 122.89 (ArC), 115.97
(ArC), 113.22 (ArC), 78.58 (OCH2), 70.43 (CHOH), 58.09
(NCH2CH), 57.48 (OCH3), 43.63 (NCH2C=C), 8.05
(CH3). MS (EI): m/z (%) = 388 (21.6) [M+]. Anal. Calc.
for C17H20N6O5: C, 52.57; H, 5.19; N, 21.64; found: C,
52.41; H, 5.02; N, 21.50.
4.7.7 | 1‐(4‐chloro‐3‐methylphenoxy)‐3‐(4‐
((2‐methyl‐5‐nitro‐1H‐imidazol‐1‐yl)
methyl)‐1H‐1,2,3‐triazol‐1‐yl)propan‐2‐ol
(14 g)
4.7.5 | 1‐(2‐chlorophenoxy)‐3‐(4‐((2‐
methyl‐5‐nitro‐1H‐imidazol‐1‐yl)methyl)‐
1H‐1,2,3‐triazol‐1‐yl) propan‐2‐ol (14e)
Column Chromatography on silica gel eluted with
EtOAc afforded pure product as yellow solid (3.06 g,
78%); m.p. 106–107 °C. IR (KBr): 3225, 3125, 2900,
Column Chromatography on silica gel eluted with
EtOAc afforded pure product as white solid (3.09 g,
76%); m.p. 162–163 °C. IR (KBr): 3350, 3075, 2950,
1
1
1551, 1489, 1435, 1354, 1243, 1060, 750 cm−1. H NMR
1556, 1485, 1425, 1351, 1240, 1045, 758 cm−1. H NMR
(CDCl3, 300 MHz) δppm = 7.76 (s, 1H, C(4)‐H of imidaz-
ole), 7.71 (s, 1H, C(5)‐H of triazole), 7.37 (d, J = 7.8 Hz,
1H, aryl), 7.25–7.17 (m, 2H, aryl), 6.97–6.87 (m, 1H,
aryl), 5.18 (s, 2H, NCH2), 4.78 (dd, J = 3.3, 14.1 Hz,
1H, OCHAHB), 4.65 (dd, J = 6.9, 14.1 Hz, 1H, OCHAHB),
4.48 (br s, 1H, OH), 4.06–3.95 (complex, 3H, NCH2CH),
2.46 (s, 3H, CH3). 13C NMR (CDCl3, 75 MHz)
δppm = 163.82 (C(2) of imidazole), 159.87 (ArC‐O),
144.23 (C(4) of triazole), 139.11 (C(5) of imidazole),
135.13 (ArC), 132.87 (C(4) of imidazole), 130.62 (ArC),
(CDCl3, 300 MHz) δppm = 7.73 (s, 1H, C(4)‐H of imidaz-
ole), 7.71 (s, 1H, C(5)‐H of triazole), 7.25–7.18 (m, 2H,
aryl), 6.76 (s, 1H, aryl), 5.21 (s, H, NCH2), 4.73
(dd, J = 3.0, 14.4 Hz, 1H, OCHAHB), 4.57 (dd, J = 6.9,
14.1 Hz, 1H, OCHAHB), 4.18 (br s, H, OH), 4.02–3.84
(complex, 3H, NCH2CH), 2.50 (s, 3H, CH3), 1.55
(s, 3H, PhCH3). 13C NMR (CDCl3, 75 MHz) δppm = 163.62
(ArC‐O), 157.21 (C(2) of imidazole), 144.30 (C(4) of tri-
azole), 139.91 (C(5) of imidazole), 139.05 (ArC‐Me),
136.10 (ArC), 132.91 (C(4) of imidazole), 130.24 (ArC‐