Method for preparing C-3 oxo substituted imidazole heterocyclic compounds
A technology of compounds and synthetic methods, applied in the fields of organic chemistry, drug combination, antibacterial drugs, etc., to achieve the effects of wide application prospect, high reaction yield and wide application range
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Embodiment 1
[0031] Example 1: Preparation of 3-phenoxy-2-phenylimidazo[1,2-a]pyridine
[0032]
[0033] Take a clean reaction bottle, add a small magnet, dry it, add 2-aminopyridine (56.5mg, 0.6mmol), 2-phenoxyacetophenone (42.5mg, 0.2mmol), cuprous iodide (0.01mmol) , 1,2-dichloroethane (1.0 mL), heated at 100° C. under oxygen for 16 hours, and the reaction solution was separated by direct column chromatography to obtain the target product (44.0 mg, yield 77%). White solid, m.p.:145-146℃. 1 H NMR (400MHz, CDCl 3 ): δ=8.07(d, J=7.6Hz, 2H), 7.75(d, J=6.8Hz, 1H), 7.66(d, J=9.2Hz, 1H), 7.41(t, J=7.2Hz, 2H ),7.28-7.35(m,3H),7.20(t,J=7.6Hz,1H),7.12(t,J=7.2Hz,1H),6.97(d,J=8.0Hz,2H),6.77(t ,J=6.8Hz,1H). 13 C NMR (100MHz, CDCl 3 ):δ=156.1,139.9,132.5,131.1,130.2,128.7,127.8,126.5,124.4,123.7,121.6,117.9,115.0,112.3.FTIR(NaCl,cm -1 ):3053.3,2985.8,1647.2,1495.6,1421.5,1390.1,1362.2,1265.3,1201.7,895.0,738.7,706.0.HR-MS(ESI):m / zcalculated for C 19 h 14 N 2 O[M+H]+: 287.1184; found 287.1...
Embodiment 2
[0034] Example 2: Preparation of 3-phenoxy-2-phenylimidazo[1,2-a]pyridine
[0035]
[0036] Take a clean reaction bottle, add a small magnet, dry it, add 2-aminopyridine (56.5mg, 0.6mmol), 2-phenoxyacetophenone (42.5mg, 0.2mmol), cuprous iodide (0.01 mmol) , 1,2-dichloroethane (1.0 mL), heated at 80° C. under oxygen for 16 hours, and the reaction solution was separated by direct column chromatography to obtain the target product (40.0 mg, yield 70%).
Embodiment 3
[0037] Example 3: Preparation of 3-phenoxy-2-phenylimidazo[1,2-a]pyridine
[0038]
[0039] Take a clean reaction bottle, add a small magnet, dry it, add 2-aminopyridine (56.5mg, 0.6mmol), 2-phenoxyacetophenone (42.5mg, 0.2mmol), cuprous iodide (0.01mmol) , 1,2-dichloroethane (1.0 mL), heated at 120° C. under oxygen for 16 hours, and the reaction solution was separated by direct column chromatography to obtain the target product (37.8 mg, yield 66%).
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