A convenient and mild method for 1, 2, 4-oxadiazole preparation: cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO. Issue 26 (29th June 2016)

• Record Type: Journal Article
• Authors: Baykov, Sergey; Sharonova, Tatyana; Osipyan, Angelina; Rozhkov, Sergey; Shetnev, Anton; Smirnov, Alexey
• Is Part Of: Tetrahedron letters. Volume 57:Issue 26(2016)
• Page Start: 2898
• Page End: 2900
• Publication Date: 2016-06-29
• Subjects: 1, 2, 4-Oxadiazoles -- Cyclodehydration -- Superbase system -- O-Acylamidoximes -- DMSO; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.071
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The new catalyst system for 1, 2, 4-oxadiazole preparation is described. Using the superbase catalytic system 1, 2, 4-oxadiazole formation from O -acylamidoximes takes several minutes at RT. The method can be used for a wide scope of substrates which are stable under the basic conditions. Abstract: Herein, we reported a general, convenient, and efficient synthesis of 3, 5-disubstituted-1, 2, 4-oxadiazoles via cyclodehydration of O -acylamidoximes in the superbase system MOH/DMSO (M = Li, Na, K). Excellent isolated yields (up to 98%) were attained within short reaction times (10–20 min). In addition, mild reaction conditions and a simple work-up procedure allow the synthesis of a wide range of heat-labile 1, 2, 4-oxadiazole-containing substances.