Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters

[Image: see text] Herein, a high-yielding cycloaddition reaction of β-ketoesters and azides to provide 1,2,3-triazoles is described. The reactions employing 2-unsubstituted β-ketoesters were found to provide 5-methyl-1,2,3-triazoles, whereas 2-alkyl-substituted β-ketoesters provided 5-hydroxy-1,2,3-...

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Autores principales: Pacifico, Roberta, Destro, Dario, Gillick-Healy, Malachi W., Kelly, Brian G., Adamo, Mauro F. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8419836/
https://www.ncbi.nlm.nih.gov/pubmed/34314172
http://dx.doi.org/10.1021/acs.joc.1c00778
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author Pacifico, Roberta
Destro, Dario
Gillick-Healy, Malachi W.
Kelly, Brian G.
Adamo, Mauro F. A.
author_facet Pacifico, Roberta
Destro, Dario
Gillick-Healy, Malachi W.
Kelly, Brian G.
Adamo, Mauro F. A.
author_sort Pacifico, Roberta
collection PubMed
description [Image: see text] Herein, a high-yielding cycloaddition reaction of β-ketoesters and azides to provide 1,2,3-triazoles is described. The reactions employing 2-unsubstituted β-ketoesters were found to provide 5-methyl-1,2,3-triazoles, whereas 2-alkyl-substituted β-ketoesters provided 5-hydroxy-1,2,3-triazoles (shown to be relatively acidic) in high yields and as single regioisomers. Several novel compounds were reported and characterized including long-chain 5-hydroxy-1,2,3-triazoles potentially bioisosteric to hydroxamic acids.
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spelling pubmed-84198362021-09-07 Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters Pacifico, Roberta Destro, Dario Gillick-Healy, Malachi W. Kelly, Brian G. Adamo, Mauro F. A. J Org Chem [Image: see text] Herein, a high-yielding cycloaddition reaction of β-ketoesters and azides to provide 1,2,3-triazoles is described. The reactions employing 2-unsubstituted β-ketoesters were found to provide 5-methyl-1,2,3-triazoles, whereas 2-alkyl-substituted β-ketoesters provided 5-hydroxy-1,2,3-triazoles (shown to be relatively acidic) in high yields and as single regioisomers. Several novel compounds were reported and characterized including long-chain 5-hydroxy-1,2,3-triazoles potentially bioisosteric to hydroxamic acids. American Chemical Society 2021-07-27 2021-09-03 /pmc/articles/PMC8419836/ /pubmed/34314172 http://dx.doi.org/10.1021/acs.joc.1c00778 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Pacifico, Roberta
Destro, Dario
Gillick-Healy, Malachi W.
Kelly, Brian G.
Adamo, Mauro F. A.
Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters
title Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters
title_full Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters
title_fullStr Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters
title_full_unstemmed Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters
title_short Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters
title_sort preparation of acidic 5-hydroxy-1,2,3-triazoles via the cycloaddition of aryl azides with β-ketoesters
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8419836/
https://www.ncbi.nlm.nih.gov/pubmed/34314172
http://dx.doi.org/10.1021/acs.joc.1c00778
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