|
ИСТИНА |
Войти в систему Регистрация |
ИПМех РАН |
||
Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2- a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynesстатья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Golantsov N.E., Golubenkova A.S., Festa A.A., Varlamov A.V., Voskressensky L.G.
- Журнал: Journal of Organic Chemistry
- Том: 87
- Номер: 5
- Год издания: 2022
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 3242
- Последняя страница: 3253
- DOI: 10.1021/acs.joc.1c02930
- Аннотация: The transformation of 2-imidazolines into 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines has been realized. A pseudo-three-component reaction of 2-imidazolines with terminal electron-deficient alkynes (2 equiv) first generates imidazolidines, containing an N-vinylpropargylamine fragment. The latter can then undergo a base-catalyzed domino aza-Claisen rearrangement/cyclization reaction sequence, simultaneously constructing pyrrole and pyrazine rings. The process works in a broad substrate scope, delivering pyrrolo[1,2-a]pyrazines in good to excellent yields (45-90%). This two-step approach can be carried out in a one-pot fashion without a noticeable decrease in yield. Remarkably, a three-component protocol for the introduction of two different alkynes has been also developed. © 2022 American Chemical Society. All rights reserved.
- Добавил в систему: Малошицкая Ольга Александровна