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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...

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Detalles Bibliográficos
Autores principales: Tan, Liquan, Zhou, Peng, Chen, Cui, Liu, Weibing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
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.
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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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