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An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P(2)O(5) and catalyzed by zinc bromide
A self-condensation cyclization reaction mediated by phosphorus pentoxide (P(2)O(5)) and catalyzed by zinc bromide (ZnBr(2)) is presented for the synthesis of polysubstituted 4-pyridones and 2-pyridones from β-keto amides. A variety of β-keto amides are used in this approach, and a wide range of fun...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869214/ https://www.ncbi.nlm.nih.gov/pubmed/24367433 http://dx.doi.org/10.3762/bjoc.9.304 |
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author | Tan, Liquan Zhou, Peng Chen, Cui Liu, Weibing |
author_facet | Tan, Liquan Zhou, Peng Chen, Cui Liu, Weibing |
author_sort | Tan, Liquan |
collection | PubMed |
description | A self-condensation cyclization reaction mediated by phosphorus pentoxide (P(2)O(5)) and catalyzed by zinc bromide (ZnBr(2)) is presented for the synthesis of polysubstituted 4-pyridones and 2-pyridones from β-keto amides. A variety of β-keto amides are used in this approach, and a wide range of functionalized 4-pyridones and 2-pyridones were obtained in good to excellent yields. When employing the N-aryl β-keto amides as the substrates in this protocol, 4-pyridones are resulted, however, when using N-aliphatic-substituted β-keto amides as the partners of N-aryl β-keto amides under the same conditions, 2-pyridones are afforded. |
format | Online Article Text |
id | pubmed-3869214 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-38692142013-12-23 An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P(2)O(5) and catalyzed by zinc bromide Tan, Liquan Zhou, Peng Chen, Cui Liu, Weibing Beilstein J Org Chem Full Research Paper A self-condensation cyclization reaction mediated by phosphorus pentoxide (P(2)O(5)) and catalyzed by zinc bromide (ZnBr(2)) is presented for the synthesis of polysubstituted 4-pyridones and 2-pyridones from β-keto amides. A variety of β-keto amides are used in this approach, and a wide range of functionalized 4-pyridones and 2-pyridones were obtained in good to excellent yields. When employing the N-aryl β-keto amides as the substrates in this protocol, 4-pyridones are resulted, however, when using N-aliphatic-substituted β-keto amides as the partners of N-aryl β-keto amides under the same conditions, 2-pyridones are afforded. Beilstein-Institut 2013-11-28 /pmc/articles/PMC3869214/ /pubmed/24367433 http://dx.doi.org/10.3762/bjoc.9.304 Text en Copyright © 2013, Tan et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Tan, Liquan Zhou, Peng Chen, Cui Liu, Weibing An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P(2)O(5) and catalyzed by zinc bromide |
title | An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P(2)O(5) and catalyzed by zinc bromide |
title_full | An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P(2)O(5) and catalyzed by zinc bromide |
title_fullStr | An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P(2)O(5) and catalyzed by zinc bromide |
title_full_unstemmed | An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P(2)O(5) and catalyzed by zinc bromide |
title_short | An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P(2)O(5) and catalyzed by zinc bromide |
title_sort | efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by p(2)o(5) and catalyzed by zinc bromide |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869214/ https://www.ncbi.nlm.nih.gov/pubmed/24367433 http://dx.doi.org/10.3762/bjoc.9.304 |
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