1,3,4,6-tetracarbonyl systems. Part 8. Synthesis and antimicrobial activity of 2(5)-halogenated derivatives of 1,3,4,6-tetracarbonyl compounds

Abstract

A series of 1,6-disubstituted 2,5-dibromohexan-1,3,4,6-tetraones and 2,2,5,5-tetrahalogenohexan-1,3,4,6tetraones have been obtained by the treatment of 1,6-disubstituted hexane-1,3,4,6-tetraones with bromine and chlorine. Bromination of (4Z)-6-aryl-3,4-dihydroxy-6-oxohexa-2,4-dienamides led to (2Z,4E)-2-aminocarbonyl-6-aryl-5-bromo-3,4-dihydroxy-6-oxohexa-2,4-dienoates and 6-aryl-2,5-dibromo-3,4,6-trioxohexanamides in preparative yield. The proposed structures of the reaction products were confirmed by IR, UV, 1 H and 13 C NMR, and mass spectrometry. The bacteriostatic activity and acute toxicity of the synthesized compounds have been studied. 513 0091-150X/08/4209-0513