1,3-Thiazole-5-carbaldehyde → Methyl 4-oxo-2-phenyl-3-(thiazol-5-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate

反応式

[S:1]1[C:5]([CH:6]=O)=[CH:4][N:3]=[CH:2]1.[CH:8](=[N:15]/[C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][O:19][C:20]2=[O:25])\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:26][O-:27].[Na+]>C(OCC)(=O)CC>[O:27]=[C:26]1[C:17]2[C:21]([C:20]([O:19][CH3:18])=[O:25])=[CH:22][CH:23]=[CH:24][C:16]=2[NH:15][CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]1[C:5]1[S:1][CH:2]=[N:3][CH:4]=1

参加物

実験手順

A mixture of thiazole-5-carbaldehyde (500 mg, 4 mmol), (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (960 mg, 4 mmol), sodium methanolate (375 mg, 16.1 mmol) and ethyl propionate (30 mL) were stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (4×100 mL) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 10:1 to 1:1) to give methyl 4-oxo-2-phenyl-3-(thiazol-5-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (110 mg, yield 7%). LC-MS (ESI) m/z: 379 (M+1)+.