The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones

This work describes the synthesis of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones, their tautomerism, and reactivity towards binucleophiles. These molecules are novel and convenient building-blocks for the direct construction of biologically important polycyclic pyridones via an oxazino...

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Detalles Bibliográficos
Autores principales: Viktorova, Viktoria V., Steparuk, Elena V., Obydennov, Dmitrii L., Sosnovskikh, Vyacheslav Y.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9921744/
https://www.ncbi.nlm.nih.gov/pubmed/36770952
http://dx.doi.org/10.3390/molecules28031285
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author Viktorova, Viktoria V.
Steparuk, Elena V.
Obydennov, Dmitrii L.
Sosnovskikh, Vyacheslav Y.
author_facet Viktorova, Viktoria V.
Steparuk, Elena V.
Obydennov, Dmitrii L.
Sosnovskikh, Vyacheslav Y.
author_sort Viktorova, Viktoria V.
collection PubMed
description This work describes the synthesis of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones, their tautomerism, and reactivity towards binucleophiles. These molecules are novel and convenient building-blocks for the direct construction of biologically important polycyclic pyridones via an oxazinone ring-opening transformation promoted with ammonium acetate or acetic acid. In the case of o-phenylenediamine, partial aromatization of the obtained heterocycles proceeded to form polycyclic benzimidazole-fused pyridones (33–91%).
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spelling pubmed-99217442023-02-12 The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones Viktorova, Viktoria V. Steparuk, Elena V. Obydennov, Dmitrii L. Sosnovskikh, Vyacheslav Y. Molecules Article This work describes the synthesis of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones, their tautomerism, and reactivity towards binucleophiles. These molecules are novel and convenient building-blocks for the direct construction of biologically important polycyclic pyridones via an oxazinone ring-opening transformation promoted with ammonium acetate or acetic acid. In the case of o-phenylenediamine, partial aromatization of the obtained heterocycles proceeded to form polycyclic benzimidazole-fused pyridones (33–91%). MDPI 2023-01-28 /pmc/articles/PMC9921744/ /pubmed/36770952 http://dx.doi.org/10.3390/molecules28031285 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 Article
Viktorova, Viktoria V.
Steparuk, Elena V.
Obydennov, Dmitrii L.
Sosnovskikh, Vyacheslav Y.
The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones
title The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones
title_full The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones
title_fullStr The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones
title_full_unstemmed The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones
title_short The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones
title_sort construction of polycyclic pyridones via ring-opening transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9921744/
https://www.ncbi.nlm.nih.gov/pubmed/36770952
http://dx.doi.org/10.3390/molecules28031285
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