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Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines

Dearomatization is an effective method to transform readily available N‐heterocycles into partially saturated motifs. Manipulation of dihydro‐derivatives holds great potential and provides access to a variety of semi‐saturated N‐heterocyclic building blocks. However, current strategies are limited i...

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Autores principales: Heusler, Arne, Fliege, Julian, Wagener, Tobias, Glorius, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252501/
https://www.ncbi.nlm.nih.gov/pubmed/33830616
http://dx.doi.org/10.1002/anie.202104115
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author Heusler, Arne
Fliege, Julian
Wagener, Tobias
Glorius, Frank
author_facet Heusler, Arne
Fliege, Julian
Wagener, Tobias
Glorius, Frank
author_sort Heusler, Arne
collection PubMed
description Dearomatization is an effective method to transform readily available N‐heterocycles into partially saturated motifs. Manipulation of dihydro‐derivatives holds great potential and provides access to a variety of semi‐saturated N‐heterocyclic building blocks. However, current strategies are limited in scope and the use of sensitive reagents restricts the applicability in synthetic laboratories. Herein, we report the synthesis of a broad variety of N‐substituted 1,4‐ and 1,2‐dihydropyridines by very mild and selective reduction with amine borane for the first time.
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spelling pubmed-82525012021-07-07 Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines Heusler, Arne Fliege, Julian Wagener, Tobias Glorius, Frank Angew Chem Int Ed Engl Communications Dearomatization is an effective method to transform readily available N‐heterocycles into partially saturated motifs. Manipulation of dihydro‐derivatives holds great potential and provides access to a variety of semi‐saturated N‐heterocyclic building blocks. However, current strategies are limited in scope and the use of sensitive reagents restricts the applicability in synthetic laboratories. Herein, we report the synthesis of a broad variety of N‐substituted 1,4‐ and 1,2‐dihydropyridines by very mild and selective reduction with amine borane for the first time. John Wiley and Sons Inc. 2021-05-10 2021-06-14 /pmc/articles/PMC8252501/ /pubmed/33830616 http://dx.doi.org/10.1002/anie.202104115 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Heusler, Arne
Fliege, Julian
Wagener, Tobias
Glorius, Frank
Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
title Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
title_full Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
title_fullStr Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
title_full_unstemmed Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
title_short Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
title_sort substituted dihydropyridine synthesis by dearomatization of pyridines
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252501/
https://www.ncbi.nlm.nih.gov/pubmed/33830616
http://dx.doi.org/10.1002/anie.202104115
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