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Synlett 2025; 36(04): 421-425
DOI: 10.1055/a-2106-5177
DOI: 10.1055/a-2106-5177
letter
Simple and Efficient Synthesis of Highly Functional 2-Oxonicotinonitriles from 2-Chloronicotinonitriles
This work was performed within the framework of the state task of the Ministry of Science and Higher Education of the Russian Federation (project no. FEGR-2023-0004).
Abstract
A simple strategy for the synthesis of 2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives (2-oxonicotinonitrile, 3-cyanopyridone) in good yields by substituting the halogen atom with an oxime under mild conditions was developed. The proposed approach makes it possible to avoid the problems associated with the hydrolysis of easily modified groups, since the reaction is carried out in the absence of water.
Key words
pyridines - pyridones - 2-oxo-1,2-dihydropyridine-3-carbonitrile - 2-oxonicotinonitrile - oximeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2106-5177.
- Supporting Information
Publikationsverlauf
Eingereicht: 21. Mai 2023
Angenommen nach Revision: 06. Juni 2023
Accepted Manuscript online:
06. Juni 2023
Artikel online veröffentlicht:
03. August 2023
© 2023. Thieme. All rights reserved
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- 47 General Procedure for the Synthesis of Compounds 2 and 3 Potassium tert-butoxide (1.1 mmol) was added to 4-methoxybenzaldehyde oxime (1.2 mmol) in 5 mL of anhydrous 1,4-dioxane. The mixture was stirred for 5 min. Appropriate 2-chloropyridine-3-carbonitrile 1 (1 mmol) was added, and the reaction mixture was stirred at 60 °C. for 4 h. After completion of the reaction (TLC), the solution was neutralized with 10% hydrochloric acid and diluted with 25 mL of water. The precipitation was filtered and washed with water and then with propan-2-ol. The product was purified by recrystallization from propan-2-ol. The crystalline product was then dried in a vacuum desiccator over CaCl2.