Reaction of 3,3-Dichloro-2-dichloroacetylaminoacrylonitrile with Amines

Polychlorinated enamidonitrile Cl₂CÍC(CN)NHCOCHCl₂ readily reacts with primary aromatic amines, dialkylamines, piperidine, and morpholine. The reaction is accompanied by complete elimination of chlorine atoms as chloride ions with formation of 4-cyanooxazoles having the corresponding amine residue in position 5 of the ring and a CHÍN or diaminomethyl moiety in position 2. The structure of 5-arylamino(dialkylamino)-4-cyano-2-formyloxazoles was confirmed by their acid hydrolysis, as well as by the condensation with phenylhydrazine, N-alkylrhodanines, and ethyl acetoacetate in the presence of urea.