Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters
Roberta Pacifico, Dario Destro, Malachi W. Gillick‐Healy, Brian Kelly, Mauro F. A. Adamo
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.
Topics & Concepts
ChemistryCycloadditionAlkylArylCombinatorial chemistryStructural isomerOrganic chemistryAzideMedicinal chemistryCatalysisClick Chemistry and ApplicationsChemical Synthesis and AnalysisCyclopropane Reaction Mechanisms