Synthesis 2020; 52(16): 2337-2346
DOI: 10.1055/s-0040-1708019
paper
© Georg Thieme Verlag Stuttgart · New York

An Unusual Triazole Synthesis from Aurones

Arjun Kafle
a  Molecular Biosciences Program, Middle Tennessee State University, Murfreesboro, TN 37132, United States
,
Shrijiana Bhattarai
a  Molecular Biosciences Program, Middle Tennessee State University, Murfreesboro, TN 37132, United States
,
Scott T. Handy
a  Molecular Biosciences Program, Middle Tennessee State University, Murfreesboro, TN 37132, United States
b  Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, United States   Email: Scott.Handy@mtsu.edu
› Author Affiliations
Financial support for the acquisition of the diffractometer by National Science Foundation is acknowledged (MRI program, grant ID 1626549).
Further Information

Publication History

Received: 09 January 2020

Accepted after revision: 30 March 2020

Publication Date:
20 April 2020 (online)


Abstract

Attempts to prepare azido-substituted aurones via a copper-catalyzed azidation failed to afford the desired product, but instead resulted in an unusual triazole formation reaction. Further efforts noted that copper was not required for this reaction, but simply thermal treatment with sodium azide in a polar aprotic solvent. A wide range of substitution patterns were tolerated in this reaction to afford the interesting salicyl-substituted triazoles in modest to excellent yield. While the mechanism is not yet clear, a simple elimination/cyclization pathway seems unlikely given the failure of the reaction on the corresponding thioaurones, which feature an even better thiol leaving group. Regardless, the potential utility of these easily accessible, multifunctional compounds should engender further interest and applications.

Supporting Information

 
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