Synthesis of 6-hydroxy-5,6-dihydro-2-pyrones and -pyridones by reaction of 4-aryl-6-trifluoromethyl-2-pyrones with water, hydrazine, and hydroxylamine

Synthesis of 6-hydroxy-5,6-dihydro-2-pyrones and -pyridones by reaction of 4-aryl-6-trifluoromethyl-2-pyrones with water, hydrazine, and hydroxylamine

Reactions of 4-aryl-6-trifluoromethyl-2 H -pyran-2-ones with sodium hydroxide followed by acidification provided the respective 6-hydroxy-5,6-dihydro derivatives, while the reactions of 4-aryl-6-trifluoromethyl-2 H -pyran-2-ones with hydrazine and hydroxylamine were accompanied by rearrangement to N...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2017-12, Vol.53 (12), p.1294-1301
Hauptverfasser: Usachev, Sergey A., Usachev, Boris I., Sosnovskikh, Vyacheslav Ya
Format: Artikel
Sprache:eng
Schlagworte:
Acidification
Aromatic compounds
Chemical synthesis
Chemistry
Chemistry and Materials Science
Hydroxides
Hydroxylamines
Organic Chemistry
Pharmacy
Sodium hydroxide
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Zusammenfassung:Reactions of 4-aryl-6-trifluoromethyl-2 H -pyran-2-ones with sodium hydroxide followed by acidification provided the respective 6-hydroxy-5,6-dihydro derivatives, while the reactions of 4-aryl-6-trifluoromethyl-2 H -pyran-2-ones with hydrazine and hydroxylamine were accompanied by rearrangement to N -substituted 6-hydroxy-5,6-dihydro-2-pyridones.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-018-2209-y