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Nichtsteroide Entzündungshemmer, 4 Umlagerungen von Heterocyclen, 11 Ketenoide Umlagerung und Oxidation von 2-Pyronen zu 1,4-Naphthochinon-5-alkansäuren

Nonsteroidal antiinflammatory agents, 4. Rearrangement reactions of heterocycles, 11. Ketenoid rearrangement and oxidation of 2-pyrons to 1,4-naphthoquinon-5-alkanoic acids

  • Organische Chemie Und Biochemie
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Abstract

Fused 2-pyrones4, obtained by the thermal condensation of ketones1 with reactive malonates2, rearrange above 200°C to yield condensed dihydroxynaphthalines5. The latter compounds can be oxidized to give 3-hydroxy-1,4-naphthoquinone-5-alkanoic acids. The reaction of ketone8 with magic malonates2 or chlorocarbonyl ketene9 affords the pyrones11 in low yields. The 2-pyrones11 could not be rearranged to13; a possible explanation for this behaviour is presented.

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Authors and Affiliations

  1. Institut für Organische Chemie, Abteilung für Organische Synthese, Karl-Franzens-Universität Graz, A-8010, Graz, Österreich

    Thomas Kappe & Hans Wildpanner

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  1. Thomas Kappe
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  2. Hans Wildpanner
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Additional information

Herrn Prof. emer. Dr.E. Ziegler, der vor 30 Jahren erstmals die ketenoide Reaktionsweise von Malonsäurederivaten beschrieb [16], in Dankbarkeit und Freundschaft gewidmet.

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Kappe, T., Wildpanner, H. Nichtsteroide Entzündungshemmer, 4 Umlagerungen von Heterocyclen, 11 Ketenoide Umlagerung und Oxidation von 2-Pyronen zu 1,4-Naphthochinon-5-alkansäuren. Monatsh Chem 119, 727–737 (1988). https://doi.org/10.1007/BF00809687

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  • DOI: https://doi.org/10.1007/BF00809687

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