Synthesis and Antiproliferative Activity of Polysubstituted Tetrahydropyridine and Piperidin-4-one-3-carboxylate Derivatives

A highly atom-economic one-pot multicomponent synthesis of polysubstituted tetrahydropyridines (THPs) is described. The reaction of anilines, aromatic aldehydes, and beta-keto esters proceeds in the presence of catalytic amount of zirconium tetrachloride, and the products can be further converted to the corresponding piperidin-4-one-3-carboxylates under acidic conditions. The two sets of products were evaluated for their anticancer activity and some of these compounds, particularly the piperidin-4-one-3-carboxylates have significant anticancer activity.