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Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines

1,2- and 1,4-dihydropyridines and N-substituted 2-pyridones are very important structural motifs due to their synthetic versatility and vast presence in a variety of alkaloids and bioactive molecules. In this article, we gather and summarize the catalytic and stereoselective synthesis of partially h...

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Autores principales: Comparini, Lucrezia Margherita, Pineschi, Mauro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10488975/
https://www.ncbi.nlm.nih.gov/pubmed/37687015
http://dx.doi.org/10.3390/molecules28176186
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author Comparini, Lucrezia Margherita
Pineschi, Mauro
author_facet Comparini, Lucrezia Margherita
Pineschi, Mauro
author_sort Comparini, Lucrezia Margherita
collection PubMed
description 1,2- and 1,4-dihydropyridines and N-substituted 2-pyridones are very important structural motifs due to their synthetic versatility and vast presence in a variety of alkaloids and bioactive molecules. In this article, we gather and summarize the catalytic and stereoselective synthesis of partially hydrogenated pyridines and pyridones via the dearomative reactions of pyridine derivatives up to mid-2023. The material is fundamentally organized according to the type of reactivity (electrophilic/nucleophilic) of the pyridine nucleus. The material is further sub-divided taking into account the nucleophilic species when dealing with electrophilic pyridines and considering the reactivity manifold of pyridine derivatives behaving as nucleophiles at the nitrogen site. The latter more recent approach allows for an unconventional entry to chiral N-substituted 2- and 4-pyridones in non-racemic form.
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spelling pubmed-104889752023-09-09 Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines Comparini, Lucrezia Margherita Pineschi, Mauro Molecules Review 1,2- and 1,4-dihydropyridines and N-substituted 2-pyridones are very important structural motifs due to their synthetic versatility and vast presence in a variety of alkaloids and bioactive molecules. In this article, we gather and summarize the catalytic and stereoselective synthesis of partially hydrogenated pyridines and pyridones via the dearomative reactions of pyridine derivatives up to mid-2023. The material is fundamentally organized according to the type of reactivity (electrophilic/nucleophilic) of the pyridine nucleus. The material is further sub-divided taking into account the nucleophilic species when dealing with electrophilic pyridines and considering the reactivity manifold of pyridine derivatives behaving as nucleophiles at the nitrogen site. The latter more recent approach allows for an unconventional entry to chiral N-substituted 2- and 4-pyridones in non-racemic form. MDPI 2023-08-22 /pmc/articles/PMC10488975/ /pubmed/37687015 http://dx.doi.org/10.3390/molecules28176186 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Comparini, Lucrezia Margherita
Pineschi, Mauro
Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines
title Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines
title_full Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines
title_fullStr Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines
title_full_unstemmed Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines
title_short Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines
title_sort recent progresses in the catalytic stereoselective dearomatization of pyridines
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10488975/
https://www.ncbi.nlm.nih.gov/pubmed/37687015
http://dx.doi.org/10.3390/molecules28176186
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