4.7 Article

Domino reaction of 3-(2-formylphenoxy)propenoates and amines: A novel synthesis of 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, and amines

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JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 20, 页码 7779-7782

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AMER CHEMICAL SOC
DOI: 10.1021/jo7013593

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[GRAPHICS] A novel synthesis of Hantzsch-type N-substituted 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, and amines has been developed. Salicaldehydes were treated with ethyl propiolate in the presence of N-methylmorpholine to give ethyl 3-(2-formylphenoxy)propenoates. Three equivalents of ethyl 3-(2-formylphenoxy)propenoates reacted with 1 equiv of amines under trifluoroacetic acid (TFA) catalyst to furnish the corresponding N-substituted 1,4-dihydropyridines in good to excellent yields, recovering the starting material salicaldehydes. A possible mechanism for the domino process was proposed. Furthermore, the products can be easily derived via further transformations and three of them exhibited strong fluorescence (Phi(f) = 0.36-0.63).

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