Rapid Boulton–Katritzky rearrangement of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles upon exposure to water and HCl

Kayukova, L.A.; Uzakova, A.B.; Vologzhanina, A.V.; Akatan, K.; Shaymardan, E.; Kabdrakhmanova, S.K.

Информация о цитировании статьи получена из Web of Science, Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 4 сентября 2018 г.

Авторы: Kayukova Lyudmila A., Uzakova Asem B., Vologzhanina Anna V., Akatan Kydyrmolla, Shaymardan Esbol, Kabdrakhmanova Sana K.
Журнал: Chemistry of Heterocyclic Compounds
Том: 54
Номер: 6
Год издания: 2018
Издательство: Kluwer Academic/Plenum Publishers
Местоположение издательства: United States
Первая страница: 643
Последняя страница: 649
DOI: 10.1007/s10593-018-2321-z
Аннотация: D-hemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton-Katritzky rearrangement, which is known to produce planar pyrazolines and pyrazoles upon heating in DMF at 150A degrees C or without solvent at 240A degrees C. The reactivity of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles in one type of Boulton-Katritzky rearrangement was observed at room temperature in H2O, DMF + H2O, and in the presence of HCl. Hydrolysis of 3,5-disubstituted 1,2,4-oxadiazoles under the first two conditions gave 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium benzoates, while the action of HCl on 3,5-disubstituted 1,2,4-oxadiazoles produced their hydrochlorides along with 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium chloride hydrate. Thus, the reaction afforded spiropyrazoline compounds instead of products with a planar structure.
Добавил в систему: Вологжанина Анна Владимировна

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Rapid Boulton–Katritzky rearrangement of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles upon exposure to water and HClстатья

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