Reactions of thiiranes with NH-heterocycles: III. The synthesis of N2/N4-mono- and N2/N4-dithietane-containing 5-bromo-2,4-dihydro-1,2,4-triazol-3-ones and their antidepressant activity
Klen, Elena E.,
Nikitina, Irina L.,
Khaliullin, Ferkat A.,
Rozit, Galina A.,
Nikitina, Ekaterina A.,
Gaisina, Gul’nara G.,
Samorodov, Aleksandr V.,
Pavlov, Valentin N. Publication date: 2024
DOI: 10.1007/s10593-024-03347-7
Abstract: (Figure presented.) 2-Thietane-containing 5-bromo-2,4-dihydro-1,2,4-triazol-3-ones were synthesized from 3,5-dibromo-1-(thietan-3-yl)-1,2,4-triazole by the reaction with sodium hydroxide solution followed by oxidation of the resulting 5-bromo-2-(thietan-3-yl)-1,2,4-triazol-3-one to 5-bromo-2-(1-oxothietan-3-yl)-2,4-dihydro-1,2,4-triazol-3-one and 5-bromo-2-(1,1-dioxothietan-3-yl)-2,4-dihydro-1,2,4-triazol-3-one. For the synthesis of isomeric 4-thiethane-containing 5-bromo-2,4-dihydro-1,2,4-triazol-3-ones, the protective dioxothietanyl group of 5-bromo-2-(1,1-dioxothietan-3-yl)-4-(thietan-3-yl)-1,2,4-triazol-3-one was removed by a treatment with sodium ethoxide followed by oxidation. The reactions of 2/4-thiethane-containing 5-bromo-2,4-dihydro-1,2,4-triazol-3-ones with 2-(chloromethyl)thiirane leading to the formation of regioisomeric 5-bromo-2,4-di(thietan-3-yl)-2,4-dihydro-1,2,4-triazol-3-ones were studied. 5-Bromo-2,4-di(1-oxothietan-3-yl)-2,4-dihydro-1,2,4-triazol-3-ones, 5-bromo-2,4-di(1,1-dioxothietan-3-yl)-2,4-dihydro-1,2,4-triazol-3-ones, and 5-bromo-2/4-(1-oxothietan-3-yl)-2/4-(1,1-dioxothietan-3-yl)-2,4-dihydro-1,2,4-triazol-3-ones were synthesized by oxidation reactions. A number of the synthesized compounds showed antidepressant activity. © The Author(s) 2024.
Издатель: Springer
Тип: Article
