Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization

[Image: see text] Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effect...

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Autores principales: Zhang, Haoqi, Riomet, Margaux, Roller, Alexander, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7091535/
https://www.ncbi.nlm.nih.gov/pubmed/32159354
http://dx.doi.org/10.1021/acs.orglett.0c00571
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author Zhang, Haoqi
Riomet, Margaux
Roller, Alexander
Maulide, Nuno
author_facet Zhang, Haoqi
Riomet, Margaux
Roller, Alexander
Maulide, Nuno
author_sort Zhang, Haoqi
collection PubMed
description [Image: see text] Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.
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spelling pubmed-70915352020-03-25 Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization Zhang, Haoqi Riomet, Margaux Roller, Alexander Maulide, Nuno Org Lett [Image: see text] Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform. American Chemical Society 2020-03-11 2020-03-20 /pmc/articles/PMC7091535/ /pubmed/32159354 http://dx.doi.org/10.1021/acs.orglett.0c00571 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Zhang, Haoqi
Riomet, Margaux
Roller, Alexander
Maulide, Nuno
Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
title Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
title_full Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
title_fullStr Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
title_full_unstemmed Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
title_short Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
title_sort synthesis of novel heterocycles by amide activation and umpolung cyclization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7091535/
https://www.ncbi.nlm.nih.gov/pubmed/32159354
http://dx.doi.org/10.1021/acs.orglett.0c00571
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AT rolleralexander synthesisofnovelheterocyclesbyamideactivationandumpolungcyclization
AT maulidenuno synthesisofnovelheterocyclesbyamideactivationandumpolungcyclization

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