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.
Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: An entry to 3-spiro-pyrazolidyl-oxindoles / S. Gazzotti, M. Manenti, L. Lo Presti, A. Silvani. - In: RSC ADVANCES. - ISSN 2046-2069. - 9:65(2019 Nov 20), pp. 37788-37800. [10.1039/c9ra07712j]
Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: An entry to 3-spiro-pyrazolidyl-oxindoles
S. GazzottiPrimo
Membro del Collaboration Group
;M. ManentiMembro del Collaboration Group
;L. Lo PrestiPenultimo
Membro del Collaboration Group
;A. Silvani
Ultimo
Supervision
2019
Abstract
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.File | Dimensione | Formato | |
---|---|---|---|
Gazzotti_Manenti_Lo-Presti_Silvani_RSC_Advances_2019_9_37788.pdf
accesso aperto
Descrizione: Versione pubblicata
Tipologia:
Publisher's version/PDF
Dimensione
680.64 kB
Formato
Adobe PDF
|
680.64 kB | Adobe PDF | Visualizza/Apri |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.