Facile synthesis of phosphorylated azides in ionic liquids and their use in the preparation of 1,2,3-triazoles

✍ Scribed by Oleg I. Artyushin; Daria V. Vorob'eva; Tamara P. Vasil'eva; Sergey N. Osipov; Gerd-Volker Röschenthaler; Irina L. Odinets

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 214 KB
• Volume: 19
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20420

✦ Synopsis

Abstract

The facile general synthetic route to azidoalkylphosphonates by the nucleophilic substitution reaction in a series of bromoalkylphosphonates was elaborated, using 1‐butyl‐3‐methylimidazolium hexafluorophosphate ([bmim][PF~6~]) as a recyclable reaction medium. These azidoalkylphosphonates were used as intermediates for copper(I)‐catalyzed regioselective 1,3‐dipolar cycloaddition with a variety of alkynes to afford 4‐substituted (1__H__‐1,2,3‐triazol‐1‐yl)alkylphosphonates as potential drug candidates. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:293–300, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20420