Issue 28, 2020

Copper-catalyzed cascade three-component azide–alkyne cycloaddition/condensation/transesterification: easy access to 3-triazolylcoumarins

Abstract

A novel and efficient strategy has been developed for the synthesis of 3-triazolylcoumarins in a one-pot, copper-catalyzed multicomponent reaction involving a cascade reaction of salicylaldehydes, ethyl 2-azidoacetate, and arylacetylenes including azide–alkyne cycloaddition, Knoevenagel condensation and an intramolecular transesterification sequence mediated by a base. This one-pot procedure provides a convenient and eco-friendly method of accessing a wide range of substituted 3-trizolylcoumarins in moderate to excellent yields with a broad substrate scope. A possible mechanism for the reaction pathway was also proposed. In addition, the fluorescence properties of 3-triazolylcoumarin derivatives were also evaluated and they displayed a wide range of fluorescence emission.

Graphical abstract: Copper-catalyzed cascade three-component azide–alkyne cycloaddition/condensation/transesterification: easy access to 3-triazolylcoumarins

Supplementary files

Article information

Article type
Paper
Submitted
26 Apr 2020
Accepted
26 Jun 2020
First published
29 Jun 2020

New J. Chem., 2020,44, 12266-12273

Copper-catalyzed cascade three-component azide–alkyne cycloaddition/condensation/transesterification: easy access to 3-triazolylcoumarins

X. He, R. Li, M. Xie, J. Duan, Q. Tang and Y. Shang, New J. Chem., 2020, 44, 12266 DOI: 10.1039/D0NJ02100H

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