Collect. Czech. Chem. Commun.
2001, 66, 1809-1830
https://doi.org/10.1135/cccc20011809
Synthesis and Antifungal Activity Evaluation of 3-Hetaryl-2,5-dihydrofuran-2-ones. An Unusual Fragmentation of the Oxazole Ring via 2,3-Selenoxide Shift
Jiří Kuneša, Vojtěch Balšáneka, Milan Poura,* and Vladimír Buchtab
a Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic
b Department of Biological and Medicinal Sciences, Faculty of Pharmacy, Charles University, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic
Abstract
In continuing the studies on the synthesis and evaluation of antifungal activity of the analogues of (-)incrustoporine, the replacement of the phenyl moiety at C3 of the furanone ring with a hetaryl substituent was considered. Thus, a series of 5-alkyl-3-hetaryl-2,5-dihydrofuran-2-ones with the thienyl, furyl and thiazolyl moieties attached to C3 was synthesized, and the compounds subjected to antifungal activity screening. In the preparation of compounds containing the oxazolyl fragment, the [2,3]-sigmatropic rearrangement led to the fragmentation of the oxazole ring, resulting in the formation of 3-(1-benzamido-2-oxoethylidene)-5-methyltetrahydrofuran-2-one. Somewhat surprisingly, the antifungal efficiency of the derivatives was lower in comparison with analogues containing a substituted phenyl at C3.
Keywords: (-)Incrustoporine; 2,5-Dihydrofuran-2-ones; Oxazoles; Thiophenes; Thiazoles; [2,3]-Sigmatropic rearrangement; Allylic selenoxide; Antifungal activity.
References: 24 live references.
