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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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
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author Aksenov, Nicolai A.
Aksenov, Dmitrii A.
Arutiunov, Nikolai A.
Aksenova, Daria S.
Aksenov, Alexander V.
Rubin, Michael
author_facet Aksenov, Nicolai A.
Aksenov, Dmitrii A.
Arutiunov, Nikolai A.
Aksenova, Daria S.
Aksenov, Alexander V.
Rubin, Michael
author_sort Aksenov, Nicolai A.
collection PubMed
description 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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spelling pubmed-90537182022-05-04 Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones Aksenov, Nicolai A. Aksenov, Dmitrii A. Arutiunov, Nikolai A. Aksenova, Daria S. Aksenov, Alexander V. Rubin, Michael RSC Adv Chemistry 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. The Royal Society of Chemistry 2020-05-14 /pmc/articles/PMC9053718/ /pubmed/35517232 http://dx.doi.org/10.1039/d0ra03520c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Aksenov, Nicolai A.
Aksenov, Dmitrii A.
Arutiunov, Nikolai A.
Aksenova, Daria S.
Aksenov, Alexander V.
Rubin, Michael
Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
title Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
title_full Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
title_fullStr Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
title_full_unstemmed Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
title_short Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
title_sort unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9053718/
https://www.ncbi.nlm.nih.gov/pubmed/35517232
http://dx.doi.org/10.1039/d0ra03520c
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