Butanal → 5-Butylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylsulfinyl)butyl]thiazolidine-2,4-dione

反応式

[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[C:20](=[O:21])[CH2:19][S:18][C:17]3=[O:22])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:23](=O)[CH2:24][CH2:25][CH3:26].N1CCCCC1>C(O)C>[CH:23](=[C:19]1[S:18][C:17](=[O:22])[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][S:10]([C:9]2[N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=[CH:7][CH:8]=2)=[O:11])[C:20]1=[O:21])[CH2:24][CH2:25][CH3:26]

参加物

実験手順

To a solution of 0.33 g (0.98 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylsulfinyl)butyl]thiazolidine-2,4-dione and 0.10 ml (1.1 mmol) of n-butyraldehyde in 5 ml of ethanol, 0.01 ml (0.1 mmol) of piperidine was added, followed by refluxing for 2 hours. After the reaction was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate) to yield 0.287 g (74.8%, yellow oily substance) of the desired product.