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Updated: Feb 7, 2026

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Diversa funcionalización de 2-piridinonas mediante inserción X-H catalizada por Rh(II) y transformaciones posteriores

Ekaterina Levashova¹, Maria Adamchik¹, Ilya Tatarinov^1,2

¹Institute of Chemistry, Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.

The Journal of organic chemistry

|February 5, 2026

Abstract:

Herein, we report a straightforward and diastereoselective synthetic approach to densely substituted 3-RX-dihydropyridin-2(1H)-ones. The method is based on the Rh(II)-catalyzed X-H insertion reaction of previously unreported 3-diazo-3,6-dihydropyridin-2(1H)-ones into a diverse range of X-H substrates (X = N, O, S), followed by base-promoted epimerization. The reaction exhibits broad functional group tolerance in both reaction partners and generally affords the target products in high yields. Furthermore, the resulting 3-allyloxy-substituted dihydropyridin-2-ones were shown to undergo a smooth [3,3]-sigmatropic Claisen rearrangement, providing efficient access to polysubstituted 3-oxopiperidin-2-ones with high diastereoselectivity. The observed stereochemical outcome was further rationalized by DFT calculations.

Palabras clave:

química orgánica química sintética química medicinal piridinonas reordenamiento de Claisen inserción X-H catálisis de rodio

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