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 |
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Authors: | N. M. Igidov E. N. Koz'minykh O. A. Sof'ina T. M. Shironina V. O. Koz'minykh |
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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 yeilds 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 ofStaphylococcus aureus andEscherichia coli.For Communication 2, see [1].Perm Pharmaceutical Academy, Perm, Russia; e-mail: kvo@pi.ccl.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1466–1475, November, 1999. |
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