954374-93-7Relevant articles and documents
Domino reaction of 3-(2-formylphenoxy)propenoates and amines: A novel synthesis of 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, and amines
Cui, Sun-Liang,Wang, Jun,Lin, Xu-Feng,Wang, Yan-Guang
, p. 7779 - 7782 (2008/02/12)
(Chemical Equation Presented) 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-methyimorpholine 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 (Φf = 0.36-0.63).