1,3,4,6-TETRACARBONYL COMPOUNDS. 3. SYNTHESIS, STRUCTURAL FEATURES, AND ANTIMICROBIAL ACTIVITY OF 1,6-DIARYL-3,4-DIHYDROXY-2,4-HEXADIENE-1,6-DIONES

Abstract

The Wittig reaction of 5-aryl-2,3-dihydro-2,3-furandiones with aroylmethylenetriphenylphosphoranes is regioselective and leads to the formation of 5-aryl-2-aroylmethylene-2,3-dihydro-3-furanones. In the presence of acid the products react with water, giving satisfactory yields of 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones. The latter were also obtained by the reaction of 2,3-furandiones with alkylnitroamines. The base-catalyzed condensation of 2,3-furandiones with acetophenones led to 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones, which exist in DMSO solution in equilibrium with the cyclic oxo tautomers – substituted 2-hydroxy-2,3-dihydro-3-furanones. Some of the synthesized compounds exhibit antimicrobial activity toward standard strains of Staphylococcus aureus and Escherichia coli. Authors: N. M. Igidov, E. N. Koz'minykh, O. A. Sof'ina, T. M. Shironina, and V. O. Koz'minykh. English Translation in Chemistry of Heterocyclic Compounds , 1999, 35 (11), pp 1276-1285 http://link.springer.com/article/10.1007/BF02251994