Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones

An original, facile, and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles from ortho-nitrochalcones is described. The featured transformation is a triggered Michael addition of the cyanide anion to the chalcone followed by a cascade cyclization mechanistically r...

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Detalles Bibliográficos
Autores principales: Aksenov, Nicolai A., Aksenov, Dmitrii A., Arutiunov, Nikolai A., Aksenova, Daria S., Aksenov, Alexander V., Rubin, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9053718/
https://www.ncbi.nlm.nih.gov/pubmed/35517232
http://dx.doi.org/10.1039/d0ra03520c
Descripción
Sumario:An original, facile, and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles from ortho-nitrochalcones is described. The featured transformation is a triggered Michael addition of the cyanide anion to the chalcone followed by a cascade cyclization mechanistically related to the Baeyer–Drewson reaction.

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