Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition.
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.
Harju
Kirsi
K
Viikki Drug Discovery Technology Center, Department of Pharmacy, P.O. Box 56, FIN-00014 University of Helsinki, Finland.
Vahermo
Mikko
M
Mutikainen
Ilpo
I
Yli-Kauhaluoma
Jari
J
D013678:Technology, Pharmaceutical / Q000379:methods*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D014230:Triazoles