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

ABSTRACT: 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.

SUBMITTER: Pacifico R

PROVIDER: S-EPMC8419836 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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

Pacifico Roberta R Destro Dario D Gillick-Healy Malachi W MW Kelly Brian G BG Adamo Mauro F A MFA

The Journal of organic chemistry 20210727 17

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 hy ...[more]

PMID: 34314172

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