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Peng et al. Sci China Chem July (2016) vol.59 No.7
(aromatic C–H), 2986, 2845 (aliphatic C–H), 1724 (C=O),
1596, 1546, 1506, 1489 (aromatic frame), 1291, 1266,
1167, 1096, 1072, 950, 898, 867 cm−1; 1H NMR (600 MHz,
DMSO-d6) δ: 7.69–7.64 (m, 3H, coumarin 5-H, phenyl
2,6-H), 7.48–7.42 (m, 3H, phenyl 3,4,5-H), 7.40 (d, J=8.5 Hz,
1H, idaimzole 4-H), 7.06 (d, J=8.5 Hz, 1H, imidazole 5-H),
6.90–6.82 (m, 2H, coumarin 6,8-H), 6.22 (s, 1H, coumarin
3-H), 5.63 (s, 1H, OH), 4.27–4.11 (m, 3H, coumarin-OCH2,
CHOH), 3.99–3.93 (m, 2H, imidazole-CH2), 2.40 (s, 3H,
coumarin 4-CH3) ppm; 13C NMR (150 MHz, DMSO-d6)
δ: 162.7, 160.1, 158.7, 156.8, 154.3, 152.8, 144.9, 129.6,
127.6, 124.5, 123.2, 122.2, 113.7, 105.7, 96.8, 94.2, 71.5,
68.5, 49.1, 24.5 ppm; HRMS (ESI) calcd. for C22H20N2O4
[M+H]+, 377.1501, found, 377.1504.
112.4, 111.7, 101.9, 70.4, 68.1, 49.3, 18.3 ppm; HRMS (ESI)
calcd. for C16H15N3O6 [M+H]+, 346.1039, found, 346.1038.
2.2.6 2-Butyl-4-chloro-1-(2-hydroxy-3-(4-methyl-2-oxo-
2H-chromen-7-yloxy)propyl)-1H-imidazole-5-carbaldehyde
(4e)
Compound 4e (0.117 g) was obtained as yellow solid
according to general procedure described for 4a starting
from potassium carbonate (0.166 g, 1.2 mmol), 2-butyl-
4-chloro-1H-imidazole-5-carbaldehyde (0.187 g, 1 mmol)
and compound 3 (0.232 g, 1 mmol). Yield: 28.1%; mp:
71–73 °C; IR (KBr) ν: 3408 (OH), 3096, 3025 (aromatic
C–H), 2987, 2843 (aliphatic C–H), 1725 (C=O), 1602, 1589,
1556, 1507 (aromatic frame), 1324, 1296, 1155, 1123, 1086,
1035, 889, 867 cm−1; 1H NMR (600 MHz, DMSO-d6) δ: 9.60
(s, 1H, CHO), 7.71 (d, J=8.7 Hz, 1H, coumarin 5-H), 6.99
(t, J=3.1 Hz, 2H, coumarin 6,8-H), 6.22 (s, 1H, coumarin
3-H), 5.56 (d, J=5.1 Hz, 1H, OH), 4.46 (dd, J=7.0, 2.2 Hz,
2H, coumarin-OCH2), 4.09 (d, J=5.0 Hz, 3H, CHOH, imi-
dazole-CH2), 2.41 (s, 3H, coumarin 4-CH3), 2.39 (d, J=6.6
Hz, 2H, CH2CH2CH2CH3), 1.36 (m, 2H, CH2CH2CH2CH3),
1.29 (m, 2H, CH2CH2CH2CH3), 0.89 (t, J=7.3 Hz, 3H,
CH2CH2CH2CH3) ppm; 13C NMR (150 MHz, DMSO-d6)
δ: 183.5, 161.8, 160.5, 155.2, 153.7, 151.1, 144.3, 126.9,
122.1, 113.8, 112.8, 111.7, 101.8, 71.7, 67.6, 45.6, 28.8, 26.5,
22.3, 18.5, 14.1 ppm; HRMS (ESI) calcd. for C21H23ClN2O5
[M+H]+, 419.1374, found, 419.1372.
2.2.4 7-(2-Hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)
propoxy)- 4-methyl-2H-chromen-2-one(4c)
Compound 4c (0.221 g) was obtained as yellow solid ac-
cording to general procedure described for 4a starting from
potassium carbonate (0.166 g, 1.2 mmol), 2-methyl-5-
nitro-1H-imidazole (0.127 g, 1 mmol) and compound 3
(0.232 g, 1 mmol). Yield: 61.4%; mp: 174–176 °C; IR
(KBr) ν: 3426 (OH), 3126, 3065 (aromatic C–H), 2956,
2814 (aliphatic C–H), 1714 (C=O), 1597, 1544, 1506, 1467
(aromatic frame), 1391, 1266, 1203, 1072, 1042, 997, 950,
1
844, 814 cm−1; H NMR (300 MHz, DMSO-d6) δ: 8.29 (s,
1H, imidazole 4-H), 7.73 (d, 1H, J=9 Hz, coumarin 5-H),
7.04 (d, 1H, J=6 Hz, coumarin 6-H), 6.99 (s, 1H, coumarin
8-H), 6.24 (s, 1H, coumarin 3-H), 5.69 (d, 1H, J=6 Hz,
OH), 4.26–4.22 (m, 2H, phenyl-OCH2), 4.11–4.09 (m, 3H,
CHOHCH2), 2.41 (s, 3H, imidazole 2-CH3), 2.38 (s, 3H,
coumarin 4-CH3) ppm; 13C NMR (75 MHz, DMSO-d6) δ:
161.7, 160.5, 155.1, 153.8, 146.1, 145.7, 126.9, 123.2, 113.7,
112.9, 111.7, 101.7, 70.5, 68.1, 49.8, 18.5, 13.3 ppm; HRMS
(ESI) calcd. for C17H17N3O6 [M+H]+, 360.1196, found,
360.1198.
2.2.7 7-(2-Hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)-4-
methyl-2H-chromen-2-one (5)
Compound 5 (0.171 g) was obtained as white solid according
to general procedure described for 4a starting from potassium
carbonate (0.166 g, 1.2 mmol), 1H-1,2,4-triazole (0.069 g,
1 mmol) and compound 3 (0.232 g, 1 mmol). Yield: 56.9%;
mp: 144–146 °C; IR (KBr) ν: 3412 (OH), 3110, 3070 (aro-
matic C–H), 2952, 2858 (aliphatic C–H), 1708 (C=O), 1621,
1612, 1547, 1513 (aromatic frame), 1393, 1329, 1247, 1187,
1104, 1048, 1009, 982, 745, 687 cm−1; 1H NMR (300 MHz,
DMSO-d6) δ: 8.48 (s, 1H, triazole 3-H), 7.98 (s, 1H, tria-
zole 5-H), 7.70 (d, 1H, J=3 Hz, coumarin 5-H), 7.00 (d, 1H,
J=3 Hz, coumarin 6-H), 6.98 (s, 1H, coumarin 8-H), 6.22
(s, 1H, coumarin 3-H), 5.57 (s, 1H, OH), 4.41–4.28 (m, 2H,
phenyl-OCH2), 4.24–4.21 (m, 1H, CHOH), 4.11–4.03 (m,
2H, triazole-CH2), 2.40 (s, 3H, coumarin 4-CH3) ppm; 13C
NMR (75 MHz, DMSO-d6) δ: 162.0, 160.8, 155.3, 154.0,
152.0, 145.6, 127.1, 113.9, 113.0, 111.9, 101.9, 70.9, 67.7,
52.4, 18.8 ppm; HRMS (ESI) calcd. for C15H15N3O4 [M+H]+,
302.1141, found, 302.1148.
2.2.5 7-(2-Hydroxy-3-(4-nitro-1H-imidazol-1-yl)
propoxy)-4-methyl-2H-chromen-2-one (4d)
Compound 4d (0.209 g) was obtained as yellow solid accord-
ing to general procedure described for 4a starting from potas-
sium carbonate (0.166 g, 1.2 mmol), 4-nitro-1H-imidazole
(0.113 g, 1 mmol) and compound 3 (0.232 g, 1 mmol). Yield:
60.6%; mp: 186–188 °C; IR (KBr) ν: 3428 (OH), 3136, 3075
(aromatic C–H), 2976, 2854 (aliphatic C–H), 1717 (C=O),
1607, 1574, 1546, 1497 (aromatic frame), 1374, 1316, 1276,
1159, 1092, 1031, 850, 834, 762 cm−1; 1H NMR (300 MHz,
DMSO-d6) δ: 8.23 (s, 1H, imidazole 5-H), 7.94 (s, 1H, imida-
zole 2-H), 7.79 (d, 1H, J=9 Hz, coumarin 5-H), 7.14 (d, 1H,
J=6 Hz, coumarin 6-H), 6.97 (s, 1H, coumarin 8-H), 6.22 (s,
1H, coumarin 3-H), 5.67 (d, 1H, J=6 Hz, OH), 4.29–4.26 (m,
2H, phenyl-OCH2), 4.12–4.06 (m, 3H, CHOHCH2), 2.40 (s,
3H, coumarin 4-CH3) ppm; 13C NMR (75 MHz, DMSO-d6) δ:
161.5, 160.7, 155.8, 153.1, 146.7, 145.1, 126.2, 123.7, 113.9,
2.2.8 7-(2-Hydroxy-3-(1H-tetrazol-1-yl)propoxy)-4-
methyl-2H-chromen-2-one (6a)
Compound 6a (0.638 g) was obtained as white solid ac-
cording to general procedure described for 4a starting from
potassium carbonate (0.166 g, 1.2 mmol), 1H-tetrazole