Issue 7, 2013
From the journal:

Organic & Biomolecular Chemistry

Metal-catalyzed rearrangements of 3-allenyl 3-hydroxyindolin-2-ones in the presence of halogenated reagents†

Benito Alcaide,*a   Pedro Almendros,*b   Amparo Lunaa  and  Natividad Prietoab  

* Corresponding authors

a Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain
E-mail: alcaideb@quim.ucm.es
Fax: +34-91-3944103

b Instituto de Química Orgánica General, IQOG, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006-Madrid, Spain
E-mail: Palmendros@iqog.csic.es
Fax: +34-91-5644853

Abstract

The reactions of 3-allenyl 3-hydroxyoxindoles with a variety of halogenated reagents in the presence of catalytic amounts of precious metal salts were explored. Both, rearrangement and oxycyclization reactions to give 4-(1-halovinyl)-quinolinediones or spirocyclic halooxindoles, respectively, are competitive pathways. The kind of functionalization is substrate and reaction conditions dependent.

Graphical abstract: Metal-catalyzed rearrangements of 3-allenyl 3-hydroxyindolin-2-ones in the presence of halogenated reagents

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Article information

DOI
https://doi.org/10.1039/C2OB27359D
Article type
Paper
Submitted
20 Sep 2012
Accepted
14 Dec 2012
First published
14 Dec 2012

Org. Biomol. Chem., 2013,11, 1216-1225

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Metal-catalyzed rearrangements of 3-allenyl 3-hydroxyindolin-2-ones in the presence of halogenated reagents

B. Alcaide, P. Almendros, A. Luna and N. Prieto, Org. Biomol. Chem., 2013, 11, 1216 DOI: 10.1039/C2OB27359D

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