Chemical Papers
(DMSO-d6) δ (ppm) (125 MHz): 13.2, 42.0, 52.6, 122.6,
124.6, 127.2, 128.4, 128.7, 131.1, 133.7, 138.6, 142.6,
145.5, 145.8. Anal. Calcd for C14H13FN6O2: C, 53.16; H,
4.14; N, 26.57; Found C, 53.17; H, 4.13; N, 26.54.
1‑(2‑Bromobenzyl)‑4‑((2‑methyl‑5‑nitro‑1H‑imidazol‑1‑yl)
methyl)‑1H‑1,2,3‑triazole (6j)
White solid, Yield: 82%, m.p.: 141.2–146.1 °C. IR (KBr)
ν (cm−1): 3248, 3102, 3057, 2983, 1513, 1440, 1330,
1283, 1223, 1174, 1114, 1050, 922, 873, 824, 750, 687.
1H NMR (DMSO-d6) δ (ppm) (300 MHz): 2.41 (3H, s,
CH3), 5.38 (2H, s, CH2), 5.71 (2H, s, CH2-Bn), 7.23 (1H,
d, J = 6.6 Hz, H6), 7.30–7.36(1H, dd, J = 7.5 Hz, 7.8 Hz,
H4), 7.41–7.45(1H, dd, J = 6.9 Hz, 7.2 Hz, H5), 7.70(1H,
d, J = 7.5 Hz, H3), 8.23 (1H, s, H-triazole), 8.36 (1H, s,
H-imidazole). 13C NMR (DMSO-d6) δ (ppm) (125 MHz):
13.3, 42.0, 53.5, 122.6, 123.4, 124.9, 128.7, 130.9, 131.1,
133.4, 135.0, 142.3, 145.5, 145.7. EI-MS m/z: 376 (Calcd for
C14H13BrN6O2: 376.03). Anal. Calcd for C14H13BrN6O2: C,
44.58; H, 3.47; N, 22.28; Found C, 44.48; H, 3.42; N, 22.24.
1‑(2‑Chlorobenzyl)‑4‑((2‑methyl‑5‑nitro‑1H‑imida‑
zol‑1‑yl)methyl)‑1H‑1,2,3‑triazole (6g)
White powder, Yield: 87%, m.p.: 149–152 °C. IR (KBr)
ν (cm−1): 3417, 3248, 3102, 3057, 2983, 1590, 1513,
1440, 1330, 1283, 1223, 1174, 1114, 1050, 922, 873,
824, 750, 687. 1H NMR (DMSO-d6) δ (ppm) (300 MHz):
2.41 (3H, s, CH3), 5.37 (2H, s, CH2), 5.72 (2H, s, CH2-
Bn), 7.27–7.30(1H, m, H6), 7.36–7.45(2H, m, H4, H5),
7.52–7.55(1H, m, H3), 8. 24(1H, s, H-triazole), 8.35 (1H,
s, H-imidazole). 13C NMR (125 MHz, DMSO-d6), δ ppm:
13.3, 42.0, 51.2, 122.6, 124.8, 128.2, 130.1, 131.1, 133.2,
133.4, 142.3, 145.5, 145.7. EI-MS m/z: 332.10 (Calcd for
C14H13ClN6O2: 332.08). Anal. Calcd for C14H13ClN6O2: C,
50.53; H, 3.94; N, 25.26; Found C, 50.48; H, 3.92; N, 25.24.
1‑(3‑Bromobenzyl)‑4‑((2‑methyl‑5‑nitro‑1H‑imidazol‑1‑yl)
methyl)‑1H‑1,2,3‑triazole (6k)
White solid, Yield: 88%, m.p: 157–160 °C, IR (KBr) ν
(cm−1): 3281, 3270, 2967, 2227, 2149, 1536, 1428, 1311,
1
1254, 1278, 1107, 1235, 936, 837, 786, 734. H NMR
1‑(3‑Chlorobenzyl)‑4‑((2‑methyl‑5‑nitro‑1H‑imidazol‑1‑yl)
methyl)‑1H‑1,2,3‑triazole (6h)
(DMSO-d6) δ (ppm) (300 MHz): 2.41 (3H, s, CH3), 5.37
(2H, s, CH2), 5.63 (2H, s, CH2-Bn), 7.31–7.39(2H, m,
H5,6), 7.54–7.56 (2H, m, H2,4), 8.29 (1H, s, H-triazole),
8.36 (1H, s, H-imidazole). 13C NMR (125 MHz, DMSO-d6),
δ ppm: 13.2, 42.0, 52.5, 122.3, 122.6, 124.6, 127.6, 131.2,
131.4, 131.5, 138.8, 142.6, 145.5, 145.8. Anal. Calcd for
C14H13BrN6O2: C, 44.58; H, 3.47; N, 22.28; Found C, 44.58;
H, 3.46; N, 22.27.
White solid, Yield: 86%, m.p.:126.9–128 °C. IR (KBr) ν
(cm−1): 3240, 3002, 2983, 1587, 1510, 1460, 1320, 1283,
1213, 1178, 1114, 1050, 922, 888, 828, 759, 688. 1H NMR
(DMSO-d6) δ (ppm) (300 MHz): 2.41 (3H, s, CH3), 5.37
(2H, s, CH2), 5.61 (2H, s, CH2–Bn), 7.19–7.27(2H, m,
H4,6), 7.39–7.43(2H, m, H2,5), 8.25 (1H, s, H-triazole),
8.36 (1H, s, H-imidazole). 13C NMR (DMSO-d6) δ (ppm)
(125 MHz): 13.2, 42.0, 52.6, 122.6, 124.6, 127.2, 128.4,
128.6, 131.1, 133.7, 138.6, 142.6, 145.5, 145.8. Anal. Calcd
for C14H13ClN6O2: C, 50.53; H, 3.94; N, 25.26; Found C,
50.51; H, 3.92; N, 25.24.
1‑(4‑Bromobenzyl)‑4‑((2‑methyl‑5‑nitro‑1H‑imidazol‑1‑yl)
methyl)‑1H‑1,2,3‑triazole (6l)
White solid, Yield: 81%, m.p: 179–181 °C. IR (KBr) ν
(cm−1): 3281, 3270, 2967, 2227, 2149, 1536, 1428, 1311,
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1254, 1278, 1107, 1235, 936, 837, 786, 734. H NMR
(DMSO-d6) δ (ppm) (300 MHz): 2.41 (3H, s, CH3), 5.37
(2H, s, CH2), 5.61 (2H, s, CH2–Bn),7.29 (2H, d, J=8.4 Hz,
H2,6), 7.60 (2H, d, J = 8.4 Hz, H3,5), 8.25(1H, s, H-tria-
zole), 8.36 (1H, s, H-imidazole). 13C NMR (125 MHz,
DMSO-d6), δ ppm: 13.2, 42.0, 52.5, 122.0, 122.6, 124.5,
127.6, 130.7, 132.1, 135.6, 142.5, 145.5, 145.8. Anal. Calcd
for C14H13BrN6O2: C, 44.58; H, 3.47; N, 22.28; Found C,
44.56; H, 3.46; N, 22.28.
1‑(4‑Chlorobenzyl)‑4‑((2‑methyl‑5‑nitro‑1H‑imidazol‑1‑yl)
methyl)‑1H‑1,2,3‑triazole (6i)
White solid, Yield: 74%, m.p.:184.4–185.9 °C. IR (KBr) ν
(cm−1): 3248, 3102, 3057, 2983, 1590, 1513, 1440, 1330,
1283, 1223, 1174, 1114, 1050, 922, 873, 824, 750, 687.
1H NMR (DMSO-d6) δ (ppm) (300 MHz): 2.41 (3H, s,
CH3), 5.37 (2H, s, CH2), 5.62 (2H, s, CH2–Bn),7.36 (2H,
d, J = 8.7 Hz, H2,6), 7.46 (2H, d, J = 8.7 Hz, H3,5), 8.25
(1H, s, H-triazole), 8.36 (1H, s, H-imidazole). 13C NMR
(DMSO-d6) δ (ppm) (125 MHz): 13.2, 42.0, 52.6, 122.6,
124.4, 129.2, 130.4, 133.4, 135.2, 142.5, 145.5, 145.8. Anal.
Calcd for C14H13ClN6O2: C, 50.53; H, 3.94; N, 25.26; Found
C, 50.51; H, 3.92; N, 25.24.
4‑((2‑Methyl‑5‑nitro‑1H‑imidazol‑1‑yl)methyl)‑1‑(2‑nitrobe
nzyl)‑1H‑1,2,3‑triazole (6m)
White solid, Yield: 87%, m.p.: 149–152 °C. IR (KBr) ν
(cm−1): 3112, 3064, 2996, 1510, 1430, 1372, 1322, 1282,
1245, 1197, 1136, 1096, 1054, 974, 912, 841, 777, 727,
1 3