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

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Title: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
Creators:
Kuneš, Jiří
Balšánek, Vojtěch
Pour, Milan
Buchta, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 12, pp. 1809-1830
Uncontrolled Keywords:(-)Incrustoporine, Oxazoles, 2,5-Dihydrofuran-2-ones, Antifungal activity, Thiazoles, Allylic selenoxide, [2,3]-Sigmatropic rearrangement, Thiophenes

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. <p>

Title: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
Creators:
Kuneš, Jiří
Balšánek, Vojtěch
Pour, Milan
Buchta, Vladimír
Uncontrolled Keywords:(-)Incrustoporine, Oxazoles, 2,5-Dihydrofuran-2-ones, Antifungal activity, Thiazoles, Allylic selenoxide, [2,3]-Sigmatropic rearrangement, Thiophenes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:66
Number:12
Page Range:pp. 1809-1830
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20011809UNSPECIFIED
ID Code:1897
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Kuneš, Jiří; Balšánek, Vojtěch; Pour, Milan; Buchta, Vladimír (2001) 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. Collection of Czechoslovak Chemical Communications, 66 (12). pp. 1809-1830. ISSN 0010-0765

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