Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones

[Image: see text] We report an unexpected rearrangement of 3-hydroxyoxindoles into benzoxazinones using electrochemistry. Our reaction employs mild and environmentally friendly conditions, and the benzoxazinone products are obtained in moderate to excellent yields. Mechanistic experiments suggest th...

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Autores principales: Vayer, Marie, Pastor, Miryam, Kofink, Christiane, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8762708/
https://www.ncbi.nlm.nih.gov/pubmed/34949089
http://dx.doi.org/10.1021/acs.orglett.1c03569
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author Vayer, Marie
Pastor, Miryam
Kofink, Christiane
Maulide, Nuno
author_facet Vayer, Marie
Pastor, Miryam
Kofink, Christiane
Maulide, Nuno
author_sort Vayer, Marie
collection PubMed
description [Image: see text] We report an unexpected rearrangement of 3-hydroxyoxindoles into benzoxazinones using electrochemistry. Our reaction employs mild and environmentally friendly conditions, and the benzoxazinone products are obtained in moderate to excellent yields. Mechanistic experiments suggest that a peroxide intermediate is likely involved.
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spelling pubmed-87627082022-01-18 Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones Vayer, Marie Pastor, Miryam Kofink, Christiane Maulide, Nuno Org Lett [Image: see text] We report an unexpected rearrangement of 3-hydroxyoxindoles into benzoxazinones using electrochemistry. Our reaction employs mild and environmentally friendly conditions, and the benzoxazinone products are obtained in moderate to excellent yields. Mechanistic experiments suggest that a peroxide intermediate is likely involved. American Chemical Society 2021-12-24 2022-01-14 /pmc/articles/PMC8762708/ /pubmed/34949089 http://dx.doi.org/10.1021/acs.orglett.1c03569 Text en © 2021 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 Vayer, Marie
Pastor, Miryam
Kofink, Christiane
Maulide, Nuno
Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
title Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
title_full Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
title_fullStr Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
title_full_unstemmed Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
title_short Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
title_sort electrochemical rearrangement of 3-hydroxyoxindoles into benzoxazinones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8762708/
https://www.ncbi.nlm.nih.gov/pubmed/34949089
http://dx.doi.org/10.1021/acs.orglett.1c03569
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AT pastormiryam electrochemicalrearrangementof3hydroxyoxindolesintobenzoxazinones
AT kofinkchristiane electrochemicalrearrangementof3hydroxyoxindolesintobenzoxazinones
AT maulidenuno electrochemicalrearrangementof3hydroxyoxindolesintobenzoxazinones

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