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6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone
Open AccessCommunication

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.
Molbank 2018, 2018(4), M1022; https://doi.org/10.3390/M1022
Received: 1 September 2018 / Revised: 27 September 2018 / Accepted: 29 September 2018 / Published: 1 October 2018
(This article belongs to the Section Structure Determination)
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
MDPI and ACS Style

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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