A novel trans-amination process in 3-arylamino- 5,5-dimethylcyclohex-2-en-1-one with nucleophiles and antimicrobial activity of selected products

Abstract

Reaction of dimedone with arylamines afforded the respective enaminones. Some N-acetyl derivatives were prepared. The reaction of enaminones with hydroxylamine was found to be dependent on the nature of the arylamine moiety and the molar ratio of hydroxylamine to give the mono-, di- or tri-oximes. Cyclization of the trioxime by acetic anhydride gave dihydrobenzo[c][1,2,5]oxadiazol-4(5H)-one-5-O-acetyloxime. Coupling of the synthesized enaminones with benzene diazonium chloride gave 2,4-bis-phenylhydrazones or a mixture of 2-mono hydrazones and bis-hydrazones depending on the nature of the arylamine moiety. Trans-amination of the arylamine of the bis hydrazones with hydroxylamine gave the same1,3-bis oxime derivative. The structures of the synthesized compounds were confirmed by IR, 1HNMR, 13C NMR spectra. The antimicrobial activity of some selected products showed promising results.