Regioselectivity Control in the Reaction of Cross-Conjugated Enynones with Monosubstituted Hydrazines: Original Synthesis of Luminescent 5-Styrylpyrazoles with a 1-Benzo[                    <i>d</i>                    ]thiazole Ring

Zatynatskiy, E.A.; Odin, I.S.; Gusev, D.M.; Zaiko, A.R.; Sokov, S.A.; Bunev, A.S.; Vologzhanina, A.V.; Kayumova, R.R.; Masyagutova, G.A.; Khursan, S.L.; Grabovskiy, S.A.; Golovanov, A.A.

Статья опубликована в высокорейтинговом журнале

Информация о цитировании статьи получена из Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 23 января 2026 г.

Авторы: Zatynatskiy Evgeniy A., Odin Ivan S., Gusev Dmitry M., Zaiko Anastasia R., Sokov Sergey A., Bunev Alexander S., Vologzhanina Anna V., Kayumova Regina R., Masyagutova Gulshat A., Khursan Sergey L., Grabovskiy Stanislav A., Golovanov Alexander A.
Журнал: Journal of Organic Chemistry
Год издания: 2025
Издательство: American Chemical Society
Местоположение издательства: United States
Номер статьи: acs.joc.5c02458
DOI: 10.1021/acs.joc.5c02458
Аннотация: Direct interactions of 1-arylpent-1-en-4-yn-3-ones with 2-hydrazinylbenzo[d]thiazoles lead to the formation of the mixtures of 3-styryland 5-styryl-1-(benzo[d]thiazol-2-yl)pyrazoles. Under the same conditions, 1,5-diarylpent-1-en-4-yn-3-ones give 5-aryl-3-arylethynyl-1-(benzo[d]thiazol-2-yl)-4,5-dihydro-1H-pyrazoles. We have described and estimated the highly regioselective one-pot synthetic route to luminescent 5-styrylsubstitutedpyrazoles containing thiazole and benzo[d]thiazole fragments on the basis of pent-1-en-4-yn-3-ones (cross-conjugated enynones) and 2-hydrazinylbenzo-[d]thiazoles. The synthetic protocol involves a preliminary addition of piperidine via the triple bond of pointed cross-conjugated enynones resultingin 1-(piperidin-1-yl)penta-1,4-dien-3-ones that in turn readily form 5-styryl-1-(benzo[d]thiazol-2-yl)pyrazoles with high regioselectivity in excellent yields. The proposed methodology is applicable to a wide range of 1-mono- and 1,5-disubstituted cross-conjugated enynones and monosubstituted hydrazines containing aryl and benzothiazole substituents. Theobtained substances exhibit strong luminescence activity (absolute quantum yield reaches 0.7). Structural and regiochemical aspects of the newly synthesized pyrazoles were confirmed by spectral and analytical data.
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Regioselectivity Control in the Reaction of Cross-Conjugated Enynones with Monosubstituted Hydrazines: Original Synthesis of Luminescent 5-Styrylpyrazoles with a 1-Benzo[ <i>d</i> ]thiazole Ringстатья

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