Green Oxidation of Heterocyclic Ketones with Oxone in Water.
Alessandro GiraudoEdoardo ArmanoCamillo MoranoMarco PallaviciniCristiano BolchiPublished in: The Journal of organic chemistry (2023)
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.