Synthesis of 5-halogenated 1,2,3-triazoles under stoichiometric Cu(I)-mediated azide-alkyne cycloaddition (CuAAC or 'Click Chemistry').

Abstract

Glucosylated heterocycles have been identified as potent inhibitors of glycogen phosphorylase (GP), a biomolecular target for the treatment of hyperglycemia and therefore type 2 diabetes. Several glucosylated triazoles have been evaluated as GP inhibitors and additional structures are being considered in the present study with the introduction of a substituent at the 5-position of the triazole ring. The 1,3-dipolar cycloaddition of azide and alkyne using stoichiometric amounts of Cu(I) halides favored the formation of the 5-halogenated 1,2,3-triazoles. The influence of the copper halide introduced (CuI, CuBr, or CuCl) provided different results and more specifically for the CuCl system which afforded a dimeric 5,5'-bistriazole in good yield (56%) as evidenced by crystallographic data.

• Authors: David Goyard, Jean-Pierre Praly, Sébastien Vidal
• Journal: Carbohydrate research (Carbohydr Res) Vol. 362 Pg. 79-83 (Nov 15 2012) ISSN: 1873-426X [Electronic] Netherlands
• PMID: 23124169 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 Elsevier Ltd. All rights reserved.

Chemical References

• Alkynes
• Azides
• Enzyme Inhibitors
• Hypoglycemic Agents
• Triazoles
• Copper
• Glycogen Phosphorylase

Topics

• Alkynes (chemistry)
• Azides (chemistry)
• Catalysis
• Click Chemistry
• Copper (chemistry)
• Crystallography, X-Ray
• Cycloaddition Reaction
• Enzyme Inhibitors (chemical synthesis)
• Glycogen Phosphorylase (antagonists & inhibitors)
• Halogenation
• Humans
• Hypoglycemic Agents (chemical synthesis)
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Stereoisomerism
• Triazoles (chemical synthesis)