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

Roberta Pacifico | Zendy; Dario Destro | Zendy; Malachi W. GillickHealy | Zendy; Brian Kelly | Zendy; Mauro F. A. Adamo | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

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

Author(s) -

Roberta Pacifico,

Dario Destro,

Malachi W. GillickHealy,

Brian Kelly,

Mauro F. A. Adamo

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c00778

Subject(s) - chemistry , cycloaddition , alkyl , aryl , combinatorial chemistry , structural isomer , organic chemistry , azide , medicinal chemistry , catalysis

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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research