Synthesis
DOI: 10.1055/a-2623-8823
paper

Novel Synthesis of 3-Amino-2pyrones and 3-Hydroxy-4-pyridones via Double Ring-Opening Reactions of 4-Pyrone Epoxides with Amines

1   Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B N Yeltsin, Yekaterinburg, Russian Federation (Ringgold ID: RIN64974)
,
Vktoria Viktorova
2   Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B N Yeltsin, Ekaterinburg, Russian Federation (Ringgold ID: RIN64974)
,
1   Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B N Yeltsin, Yekaterinburg, Russian Federation (Ringgold ID: RIN64974)
,
Polina Titova
1   Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B N Yeltsin, Yekaterinburg, Russian Federation (Ringgold ID: RIN64974)
,
Elena Steparuk
1   Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B N Yeltsin, Yekaterinburg, Russian Federation (Ringgold ID: RIN64974)
,
Nikita Alikin
1   Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B N Yeltsin, Yekaterinburg, Russian Federation (Ringgold ID: RIN64974)
,
Alena Simbirtseva
1   Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B N Yeltsin, Yekaterinburg, Russian Federation (Ringgold ID: RIN64974)
,
Alexandrina Kaurova
1   Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B N Yeltsin, Yekaterinburg, Russian Federation (Ringgold ID: RIN64974)
,
Oleg Eltsov
3   Institute of Chemical Engineering, Ural Federal University named after the first President of Russia B N Yeltsin, Yekaterinburg, Russian Federation (Ringgold ID: RIN64974)
› Author Affiliations

Supported by: Russian Science Foundation 22-73-10236

The general method for the synthesis of 3-amino-2-pyrones based on the domino reaction of 4-pyrone epoxides with amines has been developed. The formation of the products includes selective Michael addition, double ring-opening and facile deformylation. The nature of amine has a strong effect on the transformation governed by cyclization of polycarbonyl intermediates. The reaction with aromatic amines is followed by side dearoylation process to produce dihydropyrroles. The use of ammonium acetate as a nucleophile in DMSO provides a new reaction pathway yielding 3-hydroxy-4-pyridones. Tautomerism of the obtained products has been studied.



Publication History

Received: 16 March 2025

Accepted after revision: 28 May 2025

Accepted Manuscript online:
28 May 2025

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