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Synthesis 2017; 49(04): 891-898
DOI: 10.1055/s-0035-1562619
DOI: 10.1055/s-0035-1562619
paper
Synthesis of Oxindoles and Benzofuranones via Oxidation of 2-Heterocyclic BMIDAs
Further Information
Publication History
Received: 14 June 2016
Accepted after revision: 22 July 2016
Publication Date:
12 August 2016 (online)
Abstract
The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDA→BF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically active compounds containing the oxindole pharmacophore.
Supporting Information
- Optimization data, and 1H and 13C NMR spectra for all new compounds. Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562619.
- Supporting Information
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For representative examples see:
For representative examples see:
For examples using enzymatic catalysis, see:
For examples proceeding via 3-haloindoles, see:
For recent reviews, see: