Domino reaction of 3-(2-formylphenoxy)propenoates and amines: a novel synthesis of 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, and amines.
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 (Phif = 0.36-0.63).
Cui
Sun-Liang
SL
Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
Wang
Jun
J
Lin
Xu-Feng
XF
Wang
Yan-Guang
YG
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D004095:Dihydropyridines / Q000138:chemical synthesis*; D011422:Propionates / Q000737:chemistry*