Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs

Seath, Ciaran Paul and Fyfe, James W. B. and Molloy, John J. and Watson, Allan J. B. (2016) Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs. Synthesis. ISSN 0039-7881

[img]
Preview
Text (Seath-etal-Synthesis2016-Synthesis-of-oxindoles-and-benzofuranones)
Seath_etal_Synthesis2016_Synthesis_of_oxindoles_and_benzofuranones.pdf
Accepted Author Manuscript

Download (1MB)| Preview

    Abstract

    The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDAàBF3K) 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.