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(ꢂ2), 114.5 (ꢂ2), 108.0 (ꢂ2), 61.0, 56.2 (ꢂ2), 55.6 ppm; MS (ESI):
[M + H]+ ¼ 370.1, [M + Na]+ ¼ 392.1.
General synthetic procedures for compounds (9a–j)
An excess of hydroxylamine hydrochloride (15 mmol) was added
to a solution of compound 8a–j (1 mmol) and sodium acetate
(15 mmol) in absolute ethanol (5 mL). Aer reacting at 80 ꢀC for
2 h, the reaction was entirely nished (TLC control). Then the
mixture was added to water (20 mL) and extracted with EtOAc
(20 mL ꢂ 3). The combined organic layers were washed with
water, dried over Na2SO4, and the solvent was then evaporated
under reduced pressure. The residue was puried by column
chromatography (petroleum ether/AcOEt ¼ 2 : 1 as eluent) on
silica gel to obtain pure product.
2-(4-Fluorophenyl)-4-(3,4,5-trimethoxybenzoyl)-2H-1,2,3-tri-
azol (8e). Compound 8e was obtained from 7e as a light yellow
solid (0.27 g, 74%); mp 158–161 ꢀC; 1H NMR (600 MHz, CDCl3)
d 8.37 (s, 1H), 8.10 (m, 2H), 7.71 (s, 2H), 7.20 (m, 2H), 3.96 (s,
3H), 3.94 (s, 6H) ppm; 13C NMR (100 MHz, CDCl3) d 183.8, 162.3
(d, J ¼ 247.5 Hz), 152.9 (ꢂ2), 147.5, 143.1, 138.8 (ꢂ2), 135.7 (d, J
¼ 2.9 Hz), 131.2, 121.0 (d, J ¼ 8.3 Hz, ꢂ2), 116.4 (d, J ¼ 23.2 Hz,
ꢂ2), 107.9 (ꢂ2), 60.9, 56.2 (ꢂ2) ppm; MS (ESI): [M + H]+ ¼ 358.1,
[M + Na]+ ¼ 380.1.
2-(2-Chlorophenyl)-4-(3,4,5-trimethoxybenzoyl)-2H-1,2,3-tri-
azol (8f). Compound 8f was obtained from 7f as a light yellow
solid (0.28 g, 76%); mp 161–164 ꢀC; 1H NMR (600 MHz, CDCl3)
d 8.42 (s, 1H), 8.35 (t, J ¼ 1.9 Hz, 8.1 Hz, 1H), 8.10 (m, 1H), 7.75
(s, 2H), 7.56 (m, 1H), 7.41 (t, J ¼ 1.9 Hz, 8.1 Hz, 1H), 3.99 (s, 3H),
3.98 (s, 6H) ppm; 13C NMR (100 MHz, CDCl3) d 183.7, 153.0 (ꢂ2),
147.8, 143.2, 140.3, 139.1, 131.5, 131.1, 130.9, 123.2, 122.5,
(Z
+
E)-(2-Phenyl-2H-1,2,3-triazol-4-yl)(3,4,5-trimethoxy
phenyl)methanone oxime (9a). Compound 9a was obtained
from 8a as a white solid (0.33 g, 94%) with a 76 : 24 mixture of Z
1
ꢀ
and E isomers; mp 132–135 C; H NMR (400 MHz, CDCl3) (Z
isomer): d 9.23 (s, 1H), 8.57 (s, 1H), 8.10 (d, J ¼ 8.0 Hz, 2H), 7.49
(dd, J ¼ 7.6 Hz, 8.0 Hz, 2H), 7.38 (t, J ¼ 7.6 Hz, 1H), 6.98 (s, 1H),
3.92 (s, 3H), 3.88 (s, 6H) ppm; (E isomer): d 8.05 (d, J ¼ 7.9 Hz,
2H), 7.96 (s, 1H), 7.45 (dd, J ¼ 7.9 Hz, 2H), 7.35 (m, 1H), 6.86 (s,
1H), 3.94 (s, 3H), 3.86 (s, 6H) ppm; 1H NMR (600 MHz, d6-
DMSO) (Z isomer): d 12.26 (s, 1H), 8.67 (s, 1H), 8.03 (d, J ¼
7.9 Hz, 2H), 7.59 (t, J ¼ 7.6 Hz, 2H), 7.45 (t, J ¼ 7.1 Hz, 1H), 6.99
(s, 1H), 3.78 (s, 3H), 3.73 (s, 6H) ppm; MS (ESI): [M + H]+ ¼ 355.1,
[M + Na]+ ¼ 377.1.
117.7, 108.0 (ꢂ2), 61.0, 56.3 (ꢂ2) ppm; MS (ESI): [M + H]+
¼
374.1.
2-(4-Chlorophenyl)-4-(3,4,5-trimethoxybenzoyl)-2H-1,2,3-tri-
azol (8g). Compound 8g was obtained from 7g as a light yellow
solid (0.30 g, 81%); mp 136–140 ꢀC; 1H NMR (600 MHz, CDCl3)
d 8.40 (s, 1H), 8.11 (m, 2H), 7.72 (s, 2H), 7.50 (m, 2H), 3.98 (s,
3H), 3.96 (s, 6H) ppm; 13C NMR (100 MHz, CDCl3): d ¼ 183.7,
152.9, 147.6, 143.1, 138.9 (ꢂ2), 137.9, 134.3, 131.1, 129.7 (ꢂ2),
120.4 (ꢂ2), 107.9 (ꢂ2), 61.0, 56.2 (ꢂ2) ppm; MS (ESI): [M + H]+ ¼
374.1, [M + Na]+ ¼ 396.1.
(Z
+
E)-(2-(o-Tolyl)-2H-1,2,3-triazol-4-yl)(3,4,5-
trimethoxyphenyl)methanone oxime (9b). Compound 9b was
obtained from 8b as a white solid (0.33 g, 89%) with a 92 : 8
mixture of Z and E isomers; mp 307–310 ꢀC; 1H NMR (400 MHz,
CDCl3) (Z isomer) d 10.30 (s, 0.6H), 8.60 (s, 1H), 7.57 (d, J ¼
7.6 Hz, 1H), 7.35 (m, 3H), 6.95 (s, 2H), 3.90 (s, 3H), 3.86 (s, 6H),
2.40 (s, 3H) ppm; (E isomer) d 8.04 (s, 1H), 7.58 (m, 1H), 7.28 (m,
3H), 6.85 (s, 2H), 3.92 (s, 3H), 3.84 (s, 6H), 2.40 (s, 3H) ppm; MS
(ESI): [M + H]+ ¼ 369.2.
2-(2-Bromophenyl)-4-(3,4,5-trimethoxybenzoyl)-2H-1,2,3-tri-
azol (8h). Compound 8h was obtained from 7h as a light yellow
solid (0.30 g, 73%); mp 168–172 ꢀC; 1H NMR (600 MHz, CDCl3)
d 8.48 (s, 1H), 7.81 (d, J ¼ 1.1 Hz, 1H), 7.79 (s, 2H), 7.64 (dd, J ¼
7.7 Hz, 1.6 Hz, 1H), 7.51 (m, 1H), 7.42 (td, J ¼ 7.7 Hz, 1.6 Hz,
1H), 3.95 (s, 3H), 3.95 (s, 6H) ppm; 13C NMR (100 MHz, CDCl3)
d 183.9, 161.4, 153.0, 147.9, 143.2, 138.8, 134.7, 134.2, 131.2
(ꢂ2), 128.3, 128.0, 118.5, 108.1 (ꢂ2), 61.0, 56.4 (ꢂ2) ppm; MS
(ESI): [M + H]+ ¼ 418.0, [M + Na]+ ¼ 440.1.
(Z
+
E)-(2-(p-Tolyl)-2H-1,2,3-triazol-4-yl)(3,4,5-
trimethoxyphenyl)methanone oxime (9c). Compound 9c was
obtained from 8c as a white solid (0.34 g, 92%) with a 82 : 18
mixture of Z and E isomers; mp 142–145 ꢀC; 1H NMR (400 MHz,
CDCl3) (Z isomer) d 8.39 (s, 1H), 8.02 (d, J ¼ 8.4 Hz, 2H), 7.77 (s,
2H), 7.33 (d, J ¼ 8.4 Hz, 2H), 3.98 (s, 3H), 3.97 (s, 6H), 2.44 (s,
3H) ppm; (E isomer) d 8.17 (s, 1H), 7.95 (d, J ¼ 8.2 Hz, 2H), 7.30
(d, J ¼ 8.2 Hz, 2H), 6.68 (s, 2H), 3.93 (s, 3H), 3.81 (s, 6H), 2.42 (s,
3H) ppm; MS (ESI): [M + H]+ ¼ 369.1, [M + Na]+ ¼ 391.1.
2-(3-Bromophenyl)-4-(3,4,5-trimethoxybenzoyl)-2H-1,2,3-tri-
azol (8i). Compound 8i was obtained from 7i as a light yellow
solid (0.32 g, 76%); mp 156–158 ꢀC; 1H NMR (600 MHz, CDCl3)
d 8.48 (s, 1H), 7.79 (s, 2H), 7.70 (dd, J ¼ 7.5 Hz, 2.0 Hz, 1H), 7.62
(dd, J ¼ 7.5 Hz, 1.6 Hz, 1H), 7.47 (m, 2H), 3.95 (s, 3H), 3.95 (s,
6H) ppm; 13C NMR (100 MHz, CDCl3) d 183.9, 153.0, 148.0,
143.1, 138.8, 137.6, 131.2, 131.2 (ꢂ2), 130.8, 129.1, 127.7, 127.6,
108.0 (ꢂ2), 61.0, 56.3 (ꢂ2) ppm; MS (ESI): [M + H]+ ¼ 418.0, [M +
Na]+ ¼ 440.0.
(Z
+
E)-(2-(4-Methoxyphenyl)-2H-1,2,3-triazol-4-yl)(3,4,5-
trimethoxyphenyl)methanone oxime (9d). Compound 9d was
obtained from 8d as a white solid (0.33 g, 87%) with a 89 : 11
mixture of Z and E isomers; mp 178–180 ꢀC; 1H NMR (400 MHz,
CDCl3) (Z isomer) d 9.80 (s, 1H); 8.57 (s, 1H); 8.08 (d, J ¼ 7.7 Hz,
2H); 7.46 (d, J ¼ 7.7 Hz, 2H); 6.97 (s, 2H); 3.93 (s, 3H); 3.88 (s,
6H), 3.48 (s, 3H) ppm; MS (ESI): [M + H]+ ¼ 385.1, [M + Na]+ ¼
407.1.
2-(4-Bromophenyl)-4-(3,4,5-trimethoxybenzoyl)-2H-1,2,3-tri-
azol (8j). Compound 8j was obtained from 7j as a light yellow
solid (0.33 g, 79%); mp 150–153 ꢀC; 1H NMR (600 MHz, CDCl3)
d 8.38 (s, 1H), 8.00 (d, J ¼ 8.0 Hz, 2H), 7.70 (s, 2H), 7.63 (d, J ¼
8.0 Hz, 2H), 3.96 (s, 3H), 3.94 (s, 6H) ppm; 13C NMR (100 MHz,
CDCl3) d 183.6, 152.9 (ꢂ2), 147.6, 143.1, 138.9, 138.3, 132.6 (ꢂ2),
131.1, 122.2, 120.6 (ꢂ2), 107.9 (ꢂ2), 60.9, 56.2 (ꢂ2) ppm; MS
(ESI): [M + H]+ ¼ 418.0, [M + Na]+ ¼ 440.0.
(Z
+
E)-(2-(4-Fluorophenyl)-2H-1,2,3-triazol-4-yl)(3,4,5-
trimethoxyphenyl)methanone oxime (9e). Compound 9e was
obtained from 8e as a white solid (0.31 g, 84%) with a 78 : 22
mixture of Z and E isomers; mp 139–147 ꢀC; 1H NMR (600 MHz,
CDCl3) (Z isomer) d 8.40 (s, 1H), 8.14 (m, 2H), 7.73 (s, 2H), 7.23
(m, 2H), 6.66 (s, 1H), 3.98 (s, 3H), 3.97 (s, 6H) ppm; (E isomer)
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RSC Adv., 2017, 7, 29103–29111 | 29109