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. Gazzotti
Primo
Membro del Collaboration Group
;
L. Lo Presti
Penultimo
Membro del Collaboration Group
;
A. Silvani
Ultimo
Supervision
2019-11-20

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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/725882
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