Cargando…
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...
Autores principales: | , , , , |
---|---|
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 |
_version_ | 1785131924596981760 |
---|---|
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. |
format | Online Article Text |
id | pubmed-10629238 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT giraudoalessandro greenoxidationofheterocyclicketoneswithoxoneinwater AT armanoedoardo greenoxidationofheterocyclicketoneswithoxoneinwater AT moranocamillo greenoxidationofheterocyclicketoneswithoxoneinwater AT pallavicinimarco greenoxidationofheterocyclicketoneswithoxoneinwater AT bolchicristiano greenoxidationofheterocyclicketoneswithoxoneinwater |