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Cascade Cleavage of Three-Membered Rings in the Reaction of D-A Cyclopropanes with 4,5-Diazaspiro[2.4]hept-4-enes: A Route to Highly Functionalized Pyrazolinesстатья
Статья опубликована в высокорейтинговом журнале
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 2019 г.
- Авторы: Novikov Roman A., Borisov Denis D., Zotova Maria A., Denisov Dmitry A., Tkachev Yaroslav V., Korolev Victor A., Shulishov Evgeny V., Tomilov Yury V.
- Журнал: Journal of Organic Chemistry
- Том: 83
- Номер: 15
- Год издания: 2018
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 7836
- Последняя страница: 7851
- DOI: 10.1021/acs.joc.8b00725
- Аннотация: A new cascade process for reactions of donor-acceptor cyclopropanes (DACs) with spiro[cyclopropane-pyrazolines] in the presence of EtAlCl2 or Ga halides is reported. The action of a Lewis acid results in DAC activation and addition of the carbocationic intermediate to the azocyclopropane system of the pyrazoline with opening of the second three-membered ring and addition of a halide anion from the Lewis acid. A specific feature of this process is that one activated cyclopropane ring activates another one, and depending on the component ratio, the process can involve two DAC molecules and one pyrazoline molecule or one DAC molecule and two pyrazoline molecules. The process is tolerant to various functional groups and occurs with a wide range of substrates to give polyfunctionalized structures based on a 2-pyrazoline moiety.
- Добавил в систему: Белая (Зотова) Мария Алексеевна