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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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
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author Storozhenko, Olga A
Festa, Alexey A
Bella Ndoutoume, Delphine R
Aksenov, Alexander V
Varlamov, Alexey V
Voskressensky, Leonid G
author_facet Storozhenko, Olga A
Festa, Alexey A
Bella Ndoutoume, Delphine R
Aksenov, Alexander V
Varlamov, Alexey V
Voskressensky, Leonid G
author_sort Storozhenko, Olga A
collection PubMed
description 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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spelling pubmed-63174252019-01-14 Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines Storozhenko, Olga A Festa, Alexey A Bella Ndoutoume, Delphine R Aksenov, Alexander V Varlamov, Alexey V Voskressensky, Leonid G Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2018-12-19 /pmc/articles/PMC6317425/ /pubmed/30643585 http://dx.doi.org/10.3762/bjoc.14.287 Text en Copyright © 2018, Storozhenko et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Storozhenko, Olga A
Festa, Alexey A
Bella Ndoutoume, Delphine R
Aksenov, Alexander V
Varlamov, Alexey V
Voskressensky, Leonid G
Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
title Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
title_full Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
title_fullStr Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
title_full_unstemmed Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
title_short Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
title_sort mn-mediated sequential three-component domino knoevenagel/cyclization/michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
topic Full Research Paper
url 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
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