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Synthesis of 4-hydroxy-2(1H)-pyridones from azomethines and substituted dialkylmalonates

Synthese von 4-Hydroxy-2(1H)-pyridonen aus Azomethinen und substituierten Dialkylmalonaten

  • Organische Chemie Und Biochemie
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Summary

The reaction of azomethines4 with substituted dialkyl malonates5 leads to the formation of 3-substituted 4-hydroxy-2(1H)-pyridones6 in moderate yields. The azomethines4 are preparedvia arylaminopropionitriles3 or in the conventional way by acid catalyzed condensation of ketones1 with anilines2. Chlorination of pyridones6 with sulfuryl chloride leads to compounds8–10.

Zusammenfassung

Umsetzung der Azomethine4 mit den substituierten Dialkylmalonaten5 ergibt die in 3-Stellung substituierten 4-Hydroxy-2(1H)-pyridone6 in mäßigen Ausbeuten. Die Azomethine4 werden entweder über dieStrecker-Verbindungen3 oder konventionell über durch Säuren katalysierte Kondensation der Ketone1 mit den Aminen2 hergestellt. Chlorierung der Pyridone6 mit Sulfurylchlorid führt zu den Verbindungen8–10.

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Authors and Affiliations

  1. Department of Chemistry and Environmental Technology, Faculty of Technology, Technical University of Brno, CZ-76272, Zlin, Czech Republic

    S. Kafka

  2. Institute of Organic Chemistry, Karl-Franzens-University Graz, A-8010, Graz, Austria

    T. Kappe

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  1. S. Kafka
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Kafka, S., Kappe, T. Synthesis of 4-hydroxy-2(1H)-pyridones from azomethines and substituted dialkylmalonates. Monatsh Chem 128, 1019–1031 (1997). https://doi.org/10.1007/BF00806968

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  • DOI: https://doi.org/10.1007/BF00806968

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