EFFECT OF SUBSTITUENTS IN THE DIHYDROPYRIDINE RING ON THE REACTIVITY OF THE ESTER GROUP OF 3,5-DIALKOXYCARBONYL-1,4-DIHYDROPYRIDINES

Article abstract of DOI:10.1007/BF00506586

The reactivity of the ester group of 3,5-dialkoxycarbonyl-1,4-dihydropyridines upon reaction with nucleophilic reagents increases when substituents are absent in the ortho positions relative to the ester group and also in the case of steric disruption of the coplanarity of the β-aminovinylcarbonyl system when substituents are introduced at the nitrogen atom in 2,6-dimethyl derivatives.Mono- and dicarboxylic acids were obtained by hydrolysis of such esters.Thus use of esters of propiolic acid esters and arylamines in the Hantzsch synthesis made it possible to obtain 1-aryl-2,6-unsubstituted derivatives of 1,4-dihydropyridine.