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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• 作者：Sun-Liang Cui ; Jun Wang ; Xu-Feng Lin ; Yan-Guang Wang
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：September 28, 2007
• 年：2007
• 卷：72
• 期：20
• 页码：7779 - 7782
• 全文大小：106K
• 年卷期：v.72,no.20(September 28, 2007)
• ISSN：1520-6904

文摘

3593n00001>A novel synthesis of Hantzsch-type N-substituted 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, andamines has been developed. Salicaldehydes were treated withethyl propiolate in the presence of N-methylmorpholine togive ethyl 3-(2-formylphenoxy)propenoates. Three equivalents of ethyl 3-(2-formylphenoxy)propenoates reacted with1 equiv of amines under trifluoroacetic acid (TFA) catalystto furnish the corresponding N-substituted 1,4-dihydropyridines in good to excellent yields, recovering the startingmaterial salicaldehydes. A possible mechanism for thedomino process was proposed. Furthermore, the products canbe easily derived via further transformations and three ofthem exhibited strong fluorescence (_f = 0.36-0.63).