Synthesis and Chemical Properties of Derivatives of E-3-[3-(2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-yl)phenyl]propenoic Acid

By the reaction of m-aminocoric acid with maleic anhydride in an acetone medium, Z-4-{3-(E-2-carboxyethenyl)phenylamino}-4-oxo-2-butenic acid was synthesized, intramolecular cyclization of which in the presence of p-toluene sulfonic acid E-3-[3-(2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl)phenyl]propenic acid. It has been shown that the interaction of the potassium salt of m-aminocortic acid with 2-bromomethyl-1,1-dichlorocyclopropane proceeds chemoselectively while maintaining a three-membered cycle and leads to the formation of E-2,2-dichlorocyclopropylmethyl-3-(3-aminophenyl)propenoate, on the basis of which, under the sequential action of maleic and acetic anhydrides in the presence of sodium acetate, E-2,2-dichlorocyclopropylmethyl-3-[3-(2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl)phenyl]propenoate was obtained. It was found that under the action of secondary amines, it reacts with aza-Michael to form 2,2-dichlorocyclopropylmethyl-3-[3-(3-R2N-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrol-1-yl)phenyl] propenoates.