CO[C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[C:4]=1[C:11](=[O:24])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH:21][C:22]#[N:23])[CH:15]=1.[CH2:25]([NH2:28])[C:26]#[CH:27]>C1C=CC=CC=1>[CH2:25]([NH:28][C:3]1[CH:8]=[C:7]([CH3:9])[O:6][C:5](=[O:10])[C:4]=1[C:11](=[O:24])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH:21][C:22]#[N:23])[CH:15]=1)[C:26]#[CH:27]To a mixture of 0.20 g of 4-methoxy-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one and 10 ml of benzene was added 34.3 mg of propargylamine, and the mixture was heated under refluxing for 3 hours and 45 minutes. After cooling to room temperature, precipitated crystals were filtered to obtain 68.0 mg of 4-propargylamino-3-[3-[3-(2-cyanoethenyl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (20b)] as a pale brown powder.
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