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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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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. |
format | Online Article Text |
id | pubmed-9331508 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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