On the formation of seven-membered rings by arene-ynamide cyclization

ABSTRACT: A Brønsted acid-catalyzed selective arene-ynamide cyclization is described. This reaction proceeds via a keteniminium intermediate and enables the preparation of seven-membered ring enamide products. Mechanistic studies uncover an unusual product inhibition behavior. GRAPHICAL ABSTRACT: [I...

Descripción completa

Detalles Bibliográficos
Autores principales: Brutiu, Bogdan R., Bubeneck, Wilhelm Andrei, Cvetkovic, Olivera, Li, Jing, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2018
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320749/
https://www.ncbi.nlm.nih.gov/pubmed/30662090
http://dx.doi.org/10.1007/s00706-018-2320-x
Descripción
Sumario:ABSTRACT: A Brønsted acid-catalyzed selective arene-ynamide cyclization is described. This reaction proceeds via a keteniminium intermediate and enables the preparation of seven-membered ring enamide products. Mechanistic studies uncover an unusual product inhibition behavior. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-018-2320-x) contains supplementary material, which is available to authorized users.

Ejemplares similares