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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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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
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author Giraudo, Alessandro
Armano, Edoardo
Morano, Camillo
Pallavicini, Marco
Bolchi, Cristiano
author_facet Giraudo, Alessandro
Armano, Edoardo
Morano, Camillo
Pallavicini, Marco
Bolchi, Cristiano
author_sort Giraudo, Alessandro
collection PubMed
description [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.
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spelling pubmed-106292382023-11-08 Green Oxidation of Heterocyclic Ketones with Oxone in Water Giraudo, Alessandro Armano, Edoardo Morano, Camillo Pallavicini, Marco Bolchi, Cristiano J Org Chem [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. American Chemical Society 2023-10-12 /pmc/articles/PMC10629238/ /pubmed/37823876 http://dx.doi.org/10.1021/acs.joc.3c01513 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Giraudo, Alessandro
Armano, Edoardo
Morano, Camillo
Pallavicini, Marco
Bolchi, Cristiano
Green Oxidation of Heterocyclic Ketones with Oxone in Water
title Green Oxidation of Heterocyclic Ketones with Oxone in Water
title_full Green Oxidation of Heterocyclic Ketones with Oxone in Water
title_fullStr Green Oxidation of Heterocyclic Ketones with Oxone in Water
title_full_unstemmed Green Oxidation of Heterocyclic Ketones with Oxone in Water
title_short Green Oxidation of Heterocyclic Ketones with Oxone in Water
title_sort green oxidation of heterocyclic ketones with oxone in water
url 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
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