One-pot synthesis of 1, 2, 4-oxadiazoles from chalcogen amino acid derivatives under microwave irradiation. (2nd July 2021)

• Record Type: Journal Article
• Authors: Wolf, Lucas; Mayer, João C.P.; Quoos, Natália; Sauer, André C.; Schwab, Ricardo S.; Rodrigues, Oscar E.D.; Dornelles, Luciano
• Is Part Of: Tetrahedron. Volume 91(2021)
• Publication Date: 2021-07-02
• Subjects: 1, 2, 4-oxadiazoles -- Organochalcogen -- Amino acids -- Microwave -- Water; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132222
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: Image 1