Object: esters of amino- and N-alkyl(aryl)aminofumaric and N,N-dialkylaminomaleic acids, amides of Z-2-amino-3-alkoxycarbonylacrylic acids, 1-alkyl-3-alkyl(aryl)aminopyrrole-2,5-diones. Purpose: establishment of new synthetic routes to 3-(alkyl, aryl)aminopyrrole-2,5-diones by cyclization of aminoethylene-1,2-dicarboxylic acid derivatives and nucleophilic substitution of an alkylamino group in 1-alkyl-3-alkylaminopyrrole-2,5-diones with an arylamino and other amino moieties, mechanisms study of these reactions by chemical and computational methods. Methods: direct organic synthesis, chromatography, IR-, NMR 1H and 13C spectroscopy, mass-spectrometry, liquid chromatography/mass-spectrometry, elemental analysis. Results: found regularities of aminoethylene-1,2-dicarboxylic acid derivatives interaction with amines enable to purposeful synthesis of both 1-alkyl-3-aminopyrrole-2,5-dione N-derivatives with needed, also with different, substituents at both nitrogen atoms, and Z-2-amino-3-alkoxycarbonylacrylic acid amides and aminofumaric acid diamides. Novelty: new preparation protocols for 1-alkyl-3-(alkyl, dialkyl, aryl)aminopyrrole-2,5-diones, Z-2-amino-3-alkoxycarbonylacrylic acid amides and aminofumaric acid diamides have been developed; general schemes of 1-alkyl-3-alkylaminopyrrole-2,5-diones formation in the reaction of aminoethylene-1,2-dicarboxylic acids diesters with aliphatic amines and nucleophilic substitution of an alkylamino moiety in 1-alkyl-3-alkylaminopyrrole-2,5-diones by arylamines under acidic catalysis conditions have been proposed; benzenehexacarboxylic acid tri(N-methylimide) and 1,1'-dimethyl-4-methylamino-[3,3']bipyrrolyl-2,5,2',5'-tetraone were synthesized by reaction of 1-methyl-3-methylaminopyrrole-2,5-dione with hydrogen chloride. Introduction: synthesized compounds are potential plant growth regulators, pharmaceuticals and agrochemicals with extensive spectrum of activity. Field of usage: in fundamental and special courses on chemistry of heterocyclic compounds in classical universities.
