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Molbank 2018, 2018(4), M1022; https://doi.org/10.3390/M1022

Synthesis of 4-(2H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one via Ring-Switching Hydrazinolysis of 5-Ethoxymethylidenethiazolo [3,2-b][1,2,4]triazol-6-one

1
Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine
2
Department of Organic Chemistry and Pharmacy, Lesya Ukrainka Eastern European National University, Volya Avenue 13, 43025 Lutsk, Ukraine
3
Department of Chemistry, Ivano-Frankivsk National Medical University, Halytska 2, 76018 Ivano-Frankivsk, Ukraine
4
Enamine Ltd., 23 Alexandra Matrosova, 01103 Kyiv, Ukraine
5
Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland
*
Author to whom correspondence should be addressed.
Received: 1 September 2018 / Revised: 27 September 2018 / Accepted: 29 September 2018 / Published: 1 October 2018
(This article belongs to the Section Structure Determination)
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Abstract

4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation with chloroacetic acid under Williamson reaction conditions, and further one-pot cyclization–condensation with triethylorthoformate in the acetic anhydride medium, yielding compound 3. The structures of compounds 3 and 4 were confirmed by LC-MS, NMR spectra and a single X-ray diffraction analysis (for compound 4). View Full-Text
Keywords: thiazolo[3,2-b][1,2,4]triazol-6-one; ring-switch reaction; hydrazinolysis; pyrazol-3-one thiazolo[3,2-b][1,2,4]triazol-6-one; ring-switch reaction; hydrazinolysis; pyrazol-3-one
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Holota, S.; Shylych, Y.; Derkach, H.; Karpenko, O.; Gzella, A.; Lesyk, R. Synthesis of 4-(2H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one via Ring-Switching Hydrazinolysis of 5-Ethoxymethylidenethiazolo [3,2-b][1,2,4]triazol-6-one. Molbank 2018, 2018, M1022.

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