The first one-pot ambient-temperature synthesis of 1, 2, 4-oxadiazoles from amidoximes and carboxylic acid esters. Issue 7 (16th February 2017)

• Record Type: Journal Article
• Authors: Baykov, Sergey; Sharonova, Tatyana; Shetnev, Anton; Rozhkov, Sergey; Kalinin, Stanislav; Smirnov, Alexey V.
• Is Part Of: Tetrahedron. Volume 73:Issue 7(2017)
• Page Start: 945
• Page End: 951
• Publication Date: 2017-02-16
• Subjects: 1, 2, 4-Oxadiazole -- Superbase medium -- Amidoximes -- Esters -- Ambient temperature; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.01.007
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The first one-pot room-temperature protocol for the synthesis of 3, 5-disubstituted-1, 2, 4-oxadiazoles via the condensation between amidoximes and carboxylic acid esters in superbase medium MOH/DMSO is reported. A broad spectrum of alkyl, aryl and hetaryl amidoximes and esters was examined. This reaction route provides convenient access to 1, 2, 4-oxadiazoles, which is highly desirable because in the light of this privileged scaffold is recognized as an important core in the design of novel therapeutic agents and high-tech materials. Graphical abstract: Highlight: The advantages of novel protocol for 1, 2, 4-oxadiazole synthesis: high yields, mild conditions & simple work-up procedure.