SYNTHESES AND CHARACTERIZATION OF AROMATIC SECONDARY AND TERTIARY-AMINES AND A NEW IMIDAZOLONE FROM DICYANOIMIDAZOLE

Aromatic primary amines substituted with electron donating groups such as methoxy and methyl at the pam position undergo nucleophilic aromat ic substitution (SNAr) reactions on 4,5-dicyano-2-fluoro-1-methylimida zole(2) in dimethyl sulfoxide at room temperature to give secondary am ines substituted with dicyanoimidazolyl groups. Aromatic primary diami nes and hydrazine similarly react with 2 to give new secondary diamine s. Aromatic primary amines substituted with electron withdrawing group such as nitro group and also secondary amines such as carbazole react with 2 only after activation of the amine by deprotonation using sodi um hydride. The electrophilicity of 2 is high enough to react with oxy anions such as nitrite and carbonate anions and also polar aprotic sol vents via O-attack at 60 degrees C to give a new imidazolone, dicyano- 1-methyl-2-imidazolyl)-2-imidazolone(10a). W-Vis spectra of the newly synthesized compounds are described.