N. Pokhodylo, R. Savka, M. Obushak
2021
Citations
0
Influential Citations
5
Citations
Journal
Current Chemistry Letters
Abstract
Article history: Received June 1, 2020 Received in revised form June 26, 2020 Accepted July 28, 2020 Available online July 28, 2020 The new fully substituted (1H‐1,2,3-triazol-4-yl)acetic acids were synthesized from available precursors (1H‐1,2,3-triazol-4-yl)ethanones and 1Н-1,2,3-triazole-4-carboxylic acids, which are easily prepared by the Dimroth reaction from azides and 1,3-dicarbonyl compounds. The practical methods of homologization (the Arndt–Eistert reaction and homologization as a result of nucleophilic substitution by cyanide anion) and the Willgerodt-Kindler reaction were compared. The Willgerodt-Kindler method starting from (5-methyl-1H‐1,2,3-triazol-4yl)ethanones was selected as the most convenient method for the synthesis of 2-(1-aryl-5methyl-1H‐1,2,3-triazol-4-yl)acetic acids, which are promising building blocks for drug discovery. Additionally, (1H‐1,2,3-triazol-4-yl)ethanones were studied for the synthesis of alcohols, amines and in the Johnson–Corey–Chaykovsky reaction.