Affiliation:
1. Institute of Bioorganic Chemistry Russian Academy of Sciences Miklukho-Maklaya 16/10 117997 Moscow Russia
2. Pirogov Russian National Research Medical University Ostrovitianov 1 117997 Moscow Russia
Abstract
AbstractHerein 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.
Cited by
4 articles.
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1. Synthesis of Densely Substituted Pyridines through 1,2‐Oxazine‐6‐ones Inverse Electron Demand Diels–Alder Reaction;European Journal of Organic Chemistry;2023-12-18
2. Synthesis of 2H-[1,2]oxazino[3,4-c]quinoline-2,5(6H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates;Chemistry of Heterocyclic Compounds;2023-05
3. The synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones from 6-oxo-6H-1,2-oxazine-3-carboxylates;Chemistry of Heterocyclic Compounds;2023-02
4. 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;2021-09-08