Access to 4-(pyridin-2-yloxy)-1,2,4-thiadiazol-5(4H)-ones via an amidoxime O-heteroarylation/cyclization reaction sequence
Solodyankina O.V. Baykova S.O. Baykov S.V. Togyzbayeva N. Zhussupova L. Novikov M.S. Turmanov R. Boyarskiy V.P.
7 December 2025Royal Society of Chemistry
Organic and Biomolecular Chemistry
2025#23Issue 4510398 - 10407 pp.
A synthetic method was developed for the preparation of O-pyridylamidoximes in good preparative yields (up to 99%) by a reaction of the corresponding amidoximes with pyridine/quinoline N-oxides in the presence of PyBroP as an activator. Substituents in the used arylamidoxime had little effect on the yield of the target products, whereas the N-oxide structure had the greatest effect. O-Pyridyl-substituted amidoximes undergo an unusual condensation with (chlorocarbonyl)sulfenyl chloride. This transformation provides access to previously unreported 1,2,4-thiadiazol-5(4H)-ones functionalized at the N4 atom of the heterocycle by a pyridine moiety. Structural analysis of the products, combined with DFT theoretical calculations, allowed us to propose a reaction mechanism involving a key acylpyridinium intermediate. This journal is
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Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, Saint Petersburg, 199034, Russian Federation
Korkyt Ata Kyzylorda University, Aiteke Bi., Str. 29, Kyzylorda, 120014, Kazakhstan
Institute of Chemistry
Korkyt Ata Kyzylorda University
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