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Solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition
Kirsi Harju1, Mikko Vahermo, Ilpo Mutikainen
1Viikki Drug Discovery Technology Center, Department of Pharmacy, P.O. Box 56, FIN-00014 University of Helsinki, Finland.
Journal of Combinatorial Chemistry
|November 11, 2003
Summary
Solid-phase synthesis of 1,2,3-triazoles was achieved using polymer-bound azides and alkynes. This method offers a traceless approach and enables the synthesis of specific triazole derivatives for diverse applications.
Area of Science:
- Organic Chemistry
- Polymer Chemistry
- Medicinal Chemistry
Background:
- 1,2,3-triazoles are important heterocyclic compounds with broad applications.
- Solid-phase synthesis offers advantages in purification and automation.
- Developing efficient and traceless synthetic routes is crucial.
Purpose of the Study:
- To report the solid-phase synthesis of 1,2,3-triazoles.
- To develop a traceless solid-phase synthesis method.
- To synthesize specific functionalized 1,2,3-triazoles.
Main Methods:
- Solid-phase synthesis involving 1,3-dipolar cycloaddition of polymer-bound azides to alkynes.
- Preparation of polymer-bound azides from polymer-bound halides and sodium azide.
- Cleavage of synthesized triazoles using trifluoroacetic acid.
- Development of a traceless synthesis using a 2-methoxy-substituted resin.
- Synthesis of 4-hydroxybenzyl-substituted 1,2,3-triazoles from bromo-Wang resin.
Main Results:
- Successful solid-phase synthesis of 1,2,3-triazoles.
- Demonstration of a traceless solid-phase synthetic strategy.
- Efficient synthesis of polymer-bound 1,2,3-triazoles.
- Preparation of 4-hydroxybenzyl-substituted 1,2,3-triazoles.
Conclusions:
- Solid-phase synthesis is an effective method for producing 1,2,3-triazoles.
- The developed traceless method simplifies purification and reduces waste.
- The synthetic strategies allow for the preparation of diverse triazole structures.