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Polycarbonyl heterocycles. Part III. Synthesis of 2,3-furanodione derivatives by ring transformations of thiazolidine-4,5-dione derivatives

Polycarbonyl-Heterocyclen, 3. Mitt.: Synthese von 2,3-Furandion-Derivaten durch Ringtransformation von Thiazolidin-4,5-dion-Derivaten

  • Organische Chemie Und Biochemie
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Abstract

The base catalyzed isomerization of 2-(aroyl-methylene)-3-aryl-thiazolidine-4,5-dione derivatives1 leads to salts of 1-aryl-3-aroyl-4-hydroxy-pyrroline-2-thio-5-one and aliphatic amines2. It was found that2 undergo further transformation to 4-thioanilido-5-arylo-2,3-furanodione derivatives4. This series of reaction provides a convenient synthetic route to 2,3-furanodione derivatives4.

Zusammenfassung

Die basenkatalysierte Isomerisierung von 2-(Aroylmethylen)-3-aryl-thiazolidin-4,5-dionen1 führt zu Salzen von 1-Aryl-3-aroyl-4-hydroxy-pyrrolin-2-thio-5-on und aliphatischen Aminen2. Die letzteren gehen in 4-Thioanilido-5-arylo-2,3-furandion-Derivate4 über. Diese Reaktionsfolge stellte eine vorteilhafte synthetische Route zu 2,3-Furandionen dar.

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Authors and Affiliations

  1. Department of Organic Chemistry, Jagiellonian University, PL-30 060, Kraków, Poland

    Barbara Zaleska

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  1. Barbara Zaleska
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Zaleska, B. Polycarbonyl heterocycles. Part III. Synthesis of 2,3-furanodione derivatives by ring transformations of thiazolidine-4,5-dione derivatives. Monatsh Chem 117, 671–678 (1986). https://doi.org/10.1007/BF00817904

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  • DOI: https://doi.org/10.1007/BF00817904

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