One-pot synthesis of 1,2,4-oxadiazoles from chalcogen amino acid derivatives under microwave irradiation

A series of sulfur- and selenium-bearing, amino acid-derived 1,2,4-oxadiazoles were obtained by a simple procedure. The method consists of EDC-promoted coupling of chalcogen amino acid derivatives with arylamidoximes in acetone, followed by solvent removal and microwave irradiation in water medium. Influence of amidoxime substituents, of the chalcogen atom and of the amino acid side chain is discussed. The results showed this to be a fast, easy and effective method to obtain these compounds, with good functional-group tolerance, potentially favouring future applications in organic synthesis. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A series of sulfur- and selenium-bearing, amino acid-derived 1,2,4-oxadiazoles were successfully synthesized by a simple method. The results demonstrated that this approach is fast, easy to perform, and effective in obtaining the desired compounds with good functional group tolerance, potentially enabling future applications in organic synthesis.