通过芳基叠氮化物与β-酮酯的环加成反应制备酸性 5-羟基-1,2,3-三唑。
Preparation of Acidic 5-Hydroxy-1,2,3-triazoles via the Cycloaddition of Aryl Azides with β-Ketoesters.
机构信息
Centre for Synthesis and Chemical Biology (CSCB), Department of Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland.
KelAda Pharmachem Ltd., A1.01 Science Centre South, Belfield, Dublin 4, Ireland.
出版信息
J Org Chem. 2021 Sep 3;86(17):11354-11360. doi: 10.1021/acs.joc.1c00778. Epub 2021 Jul 27.
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.
本文描述了β-酮酯和叠氮化物高产率的环加成反应，以提供 1,2,3-三唑。发现反应采用 2-未取代的β-酮酯提供 5-甲基-1,2,3-三唑，而 2-烷基取代的β-酮酯以高产率和单一区域异构体提供 5-羟基-1,2,3-三唑（被证明是相对酸性的）。报道并表征了几种新型化合物，包括可能与羟肟酸具有生物等排性的长链 5-羟基-1,2,3-三唑。
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