Selective Oxidative Coupling of 3H-Pyrazol-3-ones, Isoxazol-5(2H)-ones, Pyrazolidine-3,5-diones, and Barbituric Acids with Malonyl Peroxides: An Effective C-O Functionalization

Terent'ev, A.O.; Vil', V.A.; Gorlov, E.S.; Rusina, O.N.; Korlyukov, A.A.; Nikishin, G.I.; Adam, W.

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: 22 февраля 2018 г.

Авторы: Terent'ev A.O., Vil' V.A., Gorlov E.S., Rusina O.N., Korlyukov A.A., Nikishin G.I., Adam W.
Журнал: ChemistrySelect
Том: 2
Номер: 11
Год издания: 2017
Первая страница: 3334
Последняя страница: 3341
DOI: 10.1002/slct.201700720
Аннотация: Oxidative functionalization of 3H-pyrazol-3-ones, isoxazol-5(2H)-ones, pyrazolidine-3,5-diones, and barbituric acids by malonyl peroxides results exclusively in C−O coupling products. Traditional hydroxylation, formation of carbonyl groups, or oxidative destruction of the heterocyclic ring are not observed. Under optimized reactions conditions – fluorinated alcohols as activating medium and at room temperature (20 – 25 °C) – the selective C−O coupling proceeds in high yields (up to 94 %). The oxidative insertion into the enolizable C−H bond of the substrate is mechanistically viewed as a nucleophilic attack by the heterocycle onto the electrophilically activated malonyl peroxides. For heterocyclic substrates with an active methylene group - 3H-pyrazol-3-ones, isoxazol-5(2H)-ones, and barbituric acids - both C−H bonds are oxidized to afford double oxidative C−O coupling products in good yields (up to 72 %).
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Selective Oxidative Coupling of 3H-Pyrazol-3-ones, Isoxazol-5(2H)-ones, Pyrazolidine-3,5-diones, and Barbituric Acids with Malonyl Peroxides: An Effective C-O Functionalizationстатья

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