Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition

J Comb Chem. 2003 Nov-Dec;5(6):826-33. doi: 10.1021/cc030110c.

Abstract

The solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition of polymer-bound azides to various alkynes is reported. Polymer-bound azides were synthesized from polymer-bound halides and sodium azide and reacted with alkynes to produce polymer-bound 1,2,3-triazoles. Cleavage of the triazoles was performed with trifluoroacetic acid. A traceless synthesis of 1,2,3-triazoles was developed using 2-methoxy-substituted resin (polymer-bound 4-hydroxy-2-methoxybenzyl alcohol). In addition, a synthesis of 4-hydroxybenzyl-substituted 1,2,3-triazoles from the bromo-Wang resin (4-(bromomethyl)phenoxymethyl polystyrene) was achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Technology, Pharmaceutical / methods*
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Triazoles