O-Alkylation Redirected Condensation of 5-Hydroxy-1,2-oxazine-6-ones with Primary Amines for Synthesis of 5-Hydroxyiminopyridine-2,6(1H,3H)-diones

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O-Alkylation Redirected Condensation of 5-Hydroxy-1,2-oxazine-6-ones with Primary Amines for Synthesis of 5-Hydroxyiminopyridine-2,6(1H,3H)-diones

ChemistrySelect. 2021. Vol. 6. No. 34. P. 8938–8941.

Nizovtsev A., Sokolov A., Smirnov A., Mikhaylov A. A., Myasnyanko I., Belozerova O., Baleeva N., Usmanova L., Baranov M.

Herein we report a short and general protocol for synthesis of potentially biologically active pyridine-2,6-diones. The approach is based on the redirection of the condensation of the intermediates of Dornow reaction – 5-hydroxy-1,2-oxazine-6-ones with primary amines by their prior O-alkylation. Such manipulation blocks their transformation into isoxazoles and allows one to obtain a library of 30+ previously undescribed 5-alkoxy-3-(hydroxyimino)-4-aryl-pyridine-2,6(1H,3H)-dione derivatives in 37–89 % yields.

Research target: Chemistry

Language: English

DOI

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Chemical Papers 2026

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Gurina D., Fashchevsky K. A., Oparin R. D. et al., Surfaces and Interfaces 2026 Vol. 98 Article 110545

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Novikov A., Polyhedron 2026 Vol. 299 Article 118358

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Budkov Y., Kalikin N., Journal of Chemical Physics 2026 Vol. 165 Article 064506

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Voropaeva D., S. Novikova, I. Stenina et al., Solid State Ionics 2026 Vol. 445 Article 117288

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Moshkina E., Molokeev M., Zolotov A. et al., Journal of Alloys and Compounds 2026 Vol. 1077 Article 189412

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Schneider M., Zaripov D., Dokin R. et al., Journal of Chemical Theory and Computation 2026 Vol. 22 No. 9 P. 4405–4414

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Laurinavichyute V., Levin E. E., Mironkova A. A. et al., Surfaces and Interfaces 2026 Vol. 81 Article 108389

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Filippova A. V., Yurchenko N. Y., Smirnov S. A. et al., Journal of Alloys and Compounds 2026 No. 1074 Article 189162

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