Isomerization of N-aryl substituted diethyl 3-aminoglutaconates. Part I

Article abstract of DOI:10.1016/0022-2860(95)09135-1

Diethyl acetonedicarboxylate 1 under acid catalysis reacts with aromatic amines and 2-aminonitriles 2 forming N-aryl substituted diethyl 3-aminoglutaconates 3. The structures of the products 3 were studied both in the solid and the liquid state. The presence of the double bond permits two isomeric forms. These E and Z isomers can interchange with one another under catalysis by either an acid or a base in a suitable solvent. The isomeric equilibriums were studied by ¹H NMR spectroscopy with respect to dependence on the polarity of the solvent, the temperature and the substitution present on the aromatic skeleton.