One-Pot Sequential Synthesis of β-Hydroxy-1,4-disubstituted-1,2,3-triazoles from in-situ Generated β-Azido Alcohol by Click Chemistry

Abstract

β-Hydroxy 1,2,3-triazoles from in situ generated 1,2-azidols were synthesized employing two sequential click reactions in very high yields with high regioselectivity using Cu(OAc)₂·H₂O as a catalyst in water at ambient temperature

Keywords:

• 1,2-Azidol
• Click reaction
• Cycloaddition
• Epoxide
• Ring opening
• 1,2,3-triazole

ACKNOWLEDGMENT

We thank the Council for Scientific and Industrial Research (CSIR) for financial support under the Task Force Project CMM-0006. C. U. M. and K. R. thank the CSIR and University Grants Commission (UGC) respectively for the awards of fellowships.

Notes

^a Reaction conditions: Epoxide (1.1 mmol) and sodium azide (1.0 mmol) were stirred in 3 ml of H₂O for 12–14 h and the mixture was respective alkynes and 10 mol% of Cu(OAc)₂·H₂O were added, stirred at room temperature.

^b NMR yields with respect to the corresponding azido-alcohol.