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Paper | Special issue | Vol 101, No. 2, 2020, pp.593-610
Published online, 25th September, 2019
DOI: 10.3987/COM-19-S(F)49
Expedient Routes to 1,2,4-Triazolinium Salts

Lukas Fliri, Gabriel Partl, Thomas Gelbrich, Sven Nerdinger,* Klaus Wurst, and Herwig Schottenberger

*Early Stage Development, Sandoz GmbH, Biochemiestrasse 10, 6250 Kundl, Austria

Abstract

Concomitant S-alkylation and ketazonation of thiosemicarbazide in acetone eventually led to unanticipated ring closure and formation of (3-alkylthio)-1,2,4–triazolinium salts. This initial finding was complemented by employing another three representative aldehydes and ketones. Supplementarily, some respective intermediates have been isolated by stepwise synthetic procedures. In addition to the usual spectroscopic characterization, the structures of six 1,2,4-triazolinium heterocycles, as well as two unexpected by-products thereof have been characterized by single-crystal X-ray diffraction.