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Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles

The indium-mediated allylation of novel 3-(2-Boc-hydrazono)indolin-2-one derivatives, followed by a palladium-catalysed carboamination reaction, is described to afford unprecedented spirocyclic oxindoles in good yields. The method provides an efficient access to both cis and trans diastereoisomers o...

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Autores principales: Gazzotti, Stefano, Manenti, Marco, Lo Presti, Leonardo, Silvani, Alessandra
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9075743/
https://www.ncbi.nlm.nih.gov/pubmed/35541813
http://dx.doi.org/10.1039/c9ra07712j
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author Gazzotti, Stefano
Manenti, Marco
Lo Presti, Leonardo
Silvani, Alessandra
author_facet Gazzotti, Stefano
Manenti, Marco
Lo Presti, Leonardo
Silvani, Alessandra
author_sort Gazzotti, Stefano
collection PubMed
description The indium-mediated allylation of novel 3-(2-Boc-hydrazono)indolin-2-one derivatives, followed by a palladium-catalysed carboamination reaction, is described to afford unprecedented spirocyclic oxindoles in good yields. The method provides an efficient access to both cis and trans diastereoisomers of highly functionalized compounds, bearing an N-Boc, 5-substituted pyrazolidine ring at the C3-oxindole spiro junction. The versatility of the method is fully demonstrated starting from a series of substituted isatins and employing a variety of aryl halides in the key cyclization step.
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spelling pubmed-90757432022-05-09 Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles Gazzotti, Stefano Manenti, Marco Lo Presti, Leonardo Silvani, Alessandra RSC Adv Chemistry The indium-mediated allylation of novel 3-(2-Boc-hydrazono)indolin-2-one derivatives, followed by a palladium-catalysed carboamination reaction, is described to afford unprecedented spirocyclic oxindoles in good yields. The method provides an efficient access to both cis and trans diastereoisomers of highly functionalized compounds, bearing an N-Boc, 5-substituted pyrazolidine ring at the C3-oxindole spiro junction. The versatility of the method is fully demonstrated starting from a series of substituted isatins and employing a variety of aryl halides in the key cyclization step. The Royal Society of Chemistry 2019-11-20 /pmc/articles/PMC9075743/ /pubmed/35541813 http://dx.doi.org/10.1039/c9ra07712j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Gazzotti, Stefano
Manenti, Marco
Lo Presti, Leonardo
Silvani, Alessandra
Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles
title Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles
title_full Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles
title_fullStr Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles
title_full_unstemmed Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles
title_short Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles
title_sort allylation of isatin-derived n-boc-hydrazones followed by pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9075743/
https://www.ncbi.nlm.nih.gov/pubmed/35541813
http://dx.doi.org/10.1039/c9ra07712j
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