Issue 65, 2019, Issue in Progress
From the journal:

RSC Advances

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

Stefano Gazzotti, ORCID logo a   Marco Manenti,a   Leonardo Lo Presti ORCID logo a  and  Alessandra Silvani ORCID logo *a  

* Corresponding authors

a Dipartimento di Chimica, Universitá di Milano, Via Golgi 19, Milano, Italy
E-mail: alessandra.silvani@unimi.it

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.

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

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Article information

DOI
https://doi.org/10.1039/C9RA07712J
Article type
Paper
Submitted
23 Sep 2019
Accepted
11 Nov 2019
First published
20 Nov 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 37788-37800

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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 and A. Silvani, RSC Adv., 2019, 9, 37788 DOI: 10.1039/C9RA07712J

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