![Substrate scope of the reaction. Yields are isolated yields, unless stated otherwise. [a] Determined by ¹H NMR using mesitylene as internal standard. [b] Pentane used as solvent in the first step instead of THF, and pentane:methanol=1 : 1 mixture as solvent in the second step. [c] 2.5 equiv. of Et3N and 2.2 equiv. TBSOTf used in the first step. [d] Traditional Beckmann conditions. 1) NH2OH 2) PPA[46] [e] Modified Beckmann conditions. NH2OH, thiamine hydrochloride.[47] For details, see Supporting Information.](https://www.researchgate.net/publication/381771978/figure/fig3/AS:11431281280314287@1727376555808/Substrate-scope-of-the-reaction-Yields-are-isolated-yields-unless-stated-otherwise-a_Q320.jpg)
![Control experiments and working hypothesis for the plausible mechanism of the reaction. [a] Determined by ¹H NMR using mesitylene as internal standard. For details, see Supporting Information.](https://www.researchgate.net/publication/381771978/figure/fig5/AS:11431281280344327@1727376556890/Control-experiments-and-working-hypothesis-for-the-plausible-mechanism-of-the-reaction_Q320.jpg)
August 2024
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Herein we report the development of an oxidative amination process for the streamlined synthesis of pyridones from cyclopentenones. Cyclopentenone building blocks can undergo in situ silyl enol ether formation, followed by the introduction of a nitrogen atom into the carbon skeleton with successive aromatisation to yield pyridones. The reaction sequence is operationally simple, rapid, and carried out in one pot. The reaction proceeds under mild conditions, exhibits broad functional group tolerance, complete regioselectivity, and is well scalable. The developed method provides facile access to the synthesis of ¹⁵N‐labelled targets, industrially relevant pyridone products and their derivatives in a fast and efficient way.