Efficient One-Pot, Four-Component Synthesis of 1,2,3-Triazole-Linked Tetrahydrobenzo[b]pyrans

Abstract

A one-pot procedure has been developed for the synthesis of (1,2,3-triazolyl) methoxyphenyl tetrahydro-5-oxo-4H-chromene derivatives by concurrent reaction of aryloxy propargylated aldehydes, various azides, active methylene compounds, and 1,3-cyclohexanediones using catalytic amounts of Cu(OAc)₂ / sodium ascorbate and diammonium hydrogen phosphate in aqueous ethanol media. Excellent conversion of starting materials was achieved to the desired (1,2,3-triazolyl) methoxyphenyl tetrahydro-5-oxo-4H-chromene products.

GRAPHICAL ABSTRACT

Keywords:

• 1,3-Dipolar cycloaddition
• 4H-benzo[b]pyrans
• multicomponent reaction
• 1,2,3-triazoles

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the Research Council of Shahid Beheshti University and Catalyst Center of Excellence (CCE), the University of New Brunswick, and Natural Sciences and Engineering Research Council of Canada (NSERC).

Notes

^a Isolated yield based on oxypropargylated aldehydes 1.