On the Aminolysis of Bis-Imidoylchlorides of Oxalic Acid. Part I. Reaction with Aromatic and Aliphatic Amines

Article abstract of DOI:10.1002/prac.19953370130

The reaction between bis-imidoylchlorides 2 derived from oxalic acid several aromatic and aliphatic amines was investigated.While primary aromatic amines need a thermical activation by refluxing, primary aliphatic amines give mainly at room temperature the amidines 3 in moderatly up to good yields.Proceeding from enantiomeric pure amines e.g. (R)- or (S)-1-phenylethylamine the new homochiral axalic amidines 3y and 3z with C₂-symmetry were obtained.Several secondary amines react with the bis-imidoylchloride 2a to give via intramolecular cycloacylation derivatives of isatine.The new synthesized amidines 3 perform systems with a strong molecular dynamic like prototropic and E/Z-interconversion.All new compounds described were characterized by elemental analysis and spectroscopic methods.