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One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines

Piperidine and pyrrolidine derivatives are important nitrogen heterocyclic structures with a wide range of biological activities. However, reported methods for their construction often face problems of requiring the use of expensive metal catalysts, highly toxic reaction reagents or hazardous reacti...

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Detalles Bibliográficos
Autores principales: Song, Qiao, Wang, Sheng, Lei, Xiangui, Liu, Yan, Wen, Xin, Wang, Zhouyu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9331508/
https://www.ncbi.nlm.nih.gov/pubmed/35897866
http://dx.doi.org/10.3390/molecules27154698
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author Song, Qiao
Wang, Sheng
Lei, Xiangui
Liu, Yan
Wen, Xin
Wang, Zhouyu
author_facet Song, Qiao
Wang, Sheng
Lei, Xiangui
Liu, Yan
Wen, Xin
Wang, Zhouyu
author_sort Song, Qiao
collection PubMed
description Piperidine and pyrrolidine derivatives are important nitrogen heterocyclic structures with a wide range of biological activities. However, reported methods for their construction often face problems of requiring the use of expensive metal catalysts, highly toxic reaction reagents or hazardous reaction conditions. Herein, an efficient route from halogenated amides to piperidines and pyrrolidines was disclosed. In this method, amide activation, reduction of nitrile ions, and intramolecular nucleophilic substitution were integrated in a one-pot reaction. The reaction conditions were mild and no metal catalysts were used. The synthesis of a variety of N-substituted and some C-substituted piperidines and pyrrolidines became convenient, and good yields were obtained.
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spelling pubmed-93315082022-07-29 One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines Song, Qiao Wang, Sheng Lei, Xiangui Liu, Yan Wen, Xin Wang, Zhouyu Molecules Communication Piperidine and pyrrolidine derivatives are important nitrogen heterocyclic structures with a wide range of biological activities. However, reported methods for their construction often face problems of requiring the use of expensive metal catalysts, highly toxic reaction reagents or hazardous reaction conditions. Herein, an efficient route from halogenated amides to piperidines and pyrrolidines was disclosed. In this method, amide activation, reduction of nitrile ions, and intramolecular nucleophilic substitution were integrated in a one-pot reaction. The reaction conditions were mild and no metal catalysts were used. The synthesis of a variety of N-substituted and some C-substituted piperidines and pyrrolidines became convenient, and good yields were obtained. MDPI 2022-07-22 /pmc/articles/PMC9331508/ /pubmed/35897866 http://dx.doi.org/10.3390/molecules27154698 Text en © 2022 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 Communication
Song, Qiao
Wang, Sheng
Lei, Xiangui
Liu, Yan
Wen, Xin
Wang, Zhouyu
One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines
title One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines
title_full One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines
title_fullStr One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines
title_full_unstemmed One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines
title_short One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines
title_sort one-pot route from halogenated amides to piperidines and pyrrolidines
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9331508/
https://www.ncbi.nlm.nih.gov/pubmed/35897866
http://dx.doi.org/10.3390/molecules27154698
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