Cyclization of Arylhydrazones of Cross-Conjugated Enynones: Synthesis of Luminescent Styryl-1\cyrcharCYRN-pyrazolesandPropenyl-1\cyrcharCYRN

Golovanov, A.A.; Itakhunov, R.; Odin, I.S.; Gusev, D.; Grabovskiy, S.A.; Gordon, K.V.; Vologzhanina, A.V.; Sokov, S.; Sosnin, I.M.

Авторы: Golovanov Alexander A., Itakhunov Radik, Odin Ivan S., Gusev Dmitry, Grabovskiy Stanislav A., Gordon Kareem V., Vologzhanina Anna V., Sokov Sergey, Sosnin Ilya M.
Журнал: Organic and Biomolecular Chemistry
Год издания: 2022
Издательство: Royal Society of Chemistry
Местоположение издательства: United Kingdom
DOI: 10.1039/d2ob01427k
Аннотация: Condensation of 1,5-disubstituted pent-1-en-4-yn-1-ones with arylhydrazines in acidified alcohol results mainly in the corresponding arylhydrazones with traces of the side products of cyclization at the double bond – 1,5-diaryl-3-(arylethynyl)-4,5-dihydro-1H-pyrazoles (pyrazolines). Arylhydrazones are cyclized only by reflux in high-boiling polar solvents (DMF, ethylene glycol), with the selective formation of 1,5-disubstituted 3-styrylpyrazoles with up to 77–95% yields. Thermodynamically the arylhydrazones cyclization at the triple bond is the most preferable pathway, as shown by DFT calculations and preparative synthesis experiments. Thus, we demonstrate that the reactions of arylhydrazines with 1,5-disubstituted pent-1-en-4-yn-1-ones lead to the formation of arylhydrazones and side pyrazolines impurities in a parallel (not consecutive) way. 2-Hydrazinylpyridine interacts with 1,5-disubstituted pent-1-en-4-yn-1-ones in some other way, giving not pyridinylhydrazones but 2-(5-styryl)-3-phenyl-1H-pyrazol-1-yl)pyridines (despite the medium acidity). The authors have developed the gram-scale synthesis method for these compounds with up to 60–82% yields. Besides, we have developed the synthesis method for certain styrylpyrazoles, which are quite promising substances for applying them as fluorescent probes. Their spectral-luminescent characteristics are examined as well as complexing with Hg2+, Cd2+, Pb2+ ions.
Добавил в систему: Вологжанина Анна Владимировна

	ИСТИНА	Войти в систему Регистрация
	ИСТИНА ЦЭМИ РАН
	Главная Поиск Статистика О проекте Помощь

ИСТИНА

ИСТИНА ЦЭМИ РАН

Cyclization of Arylhydrazones of Cross-Conjugated Enynones: Synthesis of Luminescent Styryl-1\cyrcharCYRN-pyrazolesandPropenyl-1\cyrcharCYRNстатья

Прикрепленные файлы