Journal of Siberian Federal University. Chemistry / Synthesis of 28-oxo-allobetulin 1,2,3-thiadiazole

Full text (.pdf)
Issue
Journal of Siberian Federal University. Chemistry. 2026 19 (1)
Authors
Levdansky, Alexander V.; Levdansky, Vladimir A.
Contact information
Levdansky, Alexander V. : Institute of Chemistry and Chemical Technology SB RAS Federal Research Center “Krasnoyarsk Scientific Center of the SB RAS” (Krasnoyarsk, Russian Federation); ; Levdansky, Vladimir A.: Institute of Chemistry and Chemical Technology SB RAS Federal Research Center “Krasnoyarsk Scientific Center of the SB RAS” (Krasnoyarsk, Russian Federation)
Keywords
28-oxo-allobetulon; 28-oxo-allobetulin 3-semicarbazone; Hurd-Mori reaction; 28-oxo-allobetulin 1,2,3-thiadiazole
Abstract

A two- step synthesis of 1,2,3-thiadiazole 28-oxo- allobetulin from 28-oxo- allobetulon was carried out for the first time. By condensation of 28-oxo- allobetulone with semicarbazide hydrochloride in an ethanol medium in the presence of potassium hydroxide, an intermediate 28-oxo- allobetulin 3-semicarbazone was obtained. Its subsequent heterocyclization using the Hurd- Mori reaction in a methylene chloride medium in the presence of thionyl chloride resulted in the production of 28-oxoallobetulin 1,2,3-thiadiazole in a yield of 78.6 %. The structure of 28-oxo- allobetulin 3-semicarbazone and 28-oxo- allobetulin 1,2,3-thiadiazole was confirmed using FTIR and NMR spectroscopy, and the composition was determined by elemental analysis

Pages
161–169
EDN
PRCYZX
Paper at repository of SibFU
https://elib.sfu-kras.ru/handle/2311/158199