Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes

Acylcyclopropanes are employed as useful donor−acceptor cyclopropanes that undergo formal (4 + 2) cyclo-condensation with N-unprotected 3-substituted indoles in thepresence of a Brønsted acid catalyst. The reaction involves thesimultaneous alkylation of both the N and C-2 positions of theindole and...

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Detalles Bibliográficos
Autores: Ortega, Alesandere, Uria Pujana, Uxue, Tejero, Tomás, Prieto Aretxabaleta, Liher, Reyes Martín, Efraim, Merino, Pedro, Vicario Hernando, José Luis
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/69960
Acceso en línea:http://hdl.handle.net/10810/69960
Access Level:acceso abierto
Palabra clave:donor−acceptor cyclopropanes
acylcyclopropanes
(4 + 2) cyclocondensation
brønsted acid catalyzed
Descripción
Sumario:Acylcyclopropanes are employed as useful donor−acceptor cyclopropanes that undergo formal (4 + 2) cyclo-condensation with N-unprotected 3-substituted indoles in thepresence of a Brønsted acid catalyst. The reaction involves thesimultaneous alkylation of both the N and C-2 positions of theindole and provides access to the 8,9-dihydropyrido[1,2-a]indolescaffold that is the central core of several biologically relevantindole alkaloids in excellent yields and good selectivities