The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates

The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates

A simple procedure was developed for the synthesis of 2 H -pyrido[3,4- c ][1,2]benzoxazine-2,4(3 H )-diones by the treatment of o -fluorophenyl-substituted 6-oxo-6 H -1,2-oxazine-3-carboxylates with primary amines. The reaction proceeded according to the mechanism previously described for the format...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2023-02, Vol.59 (1-2), p.101-104
Hauptverfasser: Ivanov, Dmitry S., Zaitseva, Elvira R., Smirnov, Alexander Yu, Nizovtsev, Alexey V., Baleeva, Nadezhda S., Baranov, Mikhail S.
Format: Artikel
Sprache:eng
Schlagworte:
Amines
Benzoxazines
Carboxylates
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
Resveratrol
Substitution reactions
Synthesis
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Zusammenfassung:A simple procedure was developed for the synthesis of 2 H -pyrido[3,4- c ][1,2]benzoxazine-2,4(3 H )-diones by the treatment of o -fluorophenyl-substituted 6-oxo-6 H -1,2-oxazine-3-carboxylates with primary amines. The reaction proceeded according to the mechanism previously described for the formation of 3-(hydroxyimino)pyridine-2,6-diones followed by intramolecular nucleophilic substitution involving the hydroxyimino group to form the 1,2-oxazine ring.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-023-03168-0