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.
Green Oxidation of Heterocyclic Ketones with Oxone in Water / A. Giraudo, E. Armano, C. Morano, M. Pallavicini, C. Bolchi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 88:21(2023 Nov 03), pp. 15461-15465. [10.1021/acs.joc.3c01513]
Green Oxidation of Heterocyclic Ketones with Oxone in Water
A. GiraudoPrimo
;E. ArmanoSecondo
;C. Morano;M. PallaviciniPenultimo
;C. Bolchi
Ultimo
2023
Abstract
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.File | Dimensione | Formato | |
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