Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines

The sequential three-component reaction between o-hydroxybenzaldehydes, N-(cyanomethyl)pyridinium salts and a nucleophile towards substituted chromenoimidazopyridines under oxidative conditions has been developed. The employment of Mn(OAc)(3)·2H(2)O or KMnO(4) as stoichiometric oxidants allowed the...

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Detalles Bibliográficos
Autores principales: Storozhenko, Olga A, Festa, Alexey A, Bella Ndoutoume, Delphine R, Aksenov, Alexander V, Varlamov, Alexey V, Voskressensky, Leonid G
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6317425/
https://www.ncbi.nlm.nih.gov/pubmed/30643585
http://dx.doi.org/10.3762/bjoc.14.287
Descripción
Sumario:The sequential three-component reaction between o-hydroxybenzaldehydes, N-(cyanomethyl)pyridinium salts and a nucleophile towards substituted chromenoimidazopyridines under oxidative conditions has been developed. The employment of Mn(OAc)(3)·2H(2)O or KMnO(4) as stoichiometric oxidants allowed the use of a wide range of nucleophiles, such as nitromethane, (aza)indoles, pyrroles, phenols, pyrazole, indazole and diethyl malonate. The formation of the target compounds presumably proceeds through a domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction sequence.

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