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Green Oxidation of Heterocyclic Ketones with Oxone in Water

[Image: see text] The recently reported efficient conversion of cyclic ketones to lactones by Oxone in neutral buffered water is extended to heterocyclic ketones, namely, cyclic N-Boc azaketones and oxoethers with the aim of obtaining N-protected azalactones and their analogues with oxygen in place...

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Detalles Bibliográficos
Autores principales: Giraudo, Alessandro, Armano, Edoardo, Morano, Camillo, Pallavicini, Marco, Bolchi, Cristiano
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10629238/
https://www.ncbi.nlm.nih.gov/pubmed/37823876
http://dx.doi.org/10.1021/acs.joc.3c01513
Descripción
Sumario:[Image: see text] The recently reported efficient conversion of cyclic ketones to lactones by Oxone in neutral buffered water is extended to heterocyclic ketones, namely, cyclic N-Boc azaketones and oxoethers with the aim of obtaining N-protected azalactones and their analogues with oxygen in place of nitrogen. N-Boc-4-piperidinone and all the cyclic oxoethers were successfully oxidized to lactones, while the azacyclic ketones with nitrogen α-positioned to carbonyl were univocally transformed into N-Boc-ω-amino acids and N-Boc-N-formyl-ω-amino acids operating in alkaline water and DMF, respectively.