Benzenepropanoic acid, 4-nitro-beta-oxo-, ethyl ester → 6-(4-Nitrophenyl)-4-oxo-2-(4-phenoxyphenyl)-1,4-dihydropyridine-3-carbonitrile
反応式
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[CH:3][C:4]#[N:5].[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([C:28](=O)[CH2:29][C:30](OCC)=[O:31])=[CH:24][CH:23]=1)([O-:21])=[O:20]>CN(C)C(=O)C>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([C:28]2[NH:1][C:2]([C:6]3[CH:11]=[CH:10][C:9]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:8][CH:7]=3)=[C:3]([C:4]#[N:5])[C:30](=[O:31])[CH:29]=2)=[CH:26][CH:27]=1)([O-:21])=[O:20]参加物
4
実験手順
A mixture of 3-amino-3-(4-phenoxyphenyl)acrylonitrile (101 mg, 0.427 mmol) and ethyl 3-(4-nitrophenyl)-3-oxopropanoate (312.8 mg, 1.319 mmol) in N,N-dimethylacetamide (1 mL) was microwaved at 230° C. for 20 min, cooled to room temperature, and concentrated. Silica gel chromatography, eluting with 0-5% methanol in dichloromethane, gave 6-(4-nitrophenyl)-4-oxo-2-(4-phenoxyphenyl)-1,4-dihydropyridine-3-carbonitrile as brown solid (211 mg, 100% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.31 (2H, δ, J=8.78 Hz), 8.19 (2H, br. s), 7.96 (2H, br. s), 7.39 (2H, t, J=7.91 Hz), 7.18 (1H, t, J=7.40 Hz), 7.06-7.13 (3H, m); MS (ES+) m/z: 410 (M+H); LC retention time: 4.275 min (analytical HPLC Method A).