Copper-catalyzed intramolecular cyclization synthesis of
2-hydroxy-indolin-3-ones: a combined experimental and theoretical study
Abstract
The synthesis of substituted 2-hydroxy-indolin-3-ones has attracted
considerable attention of synthetic chemists because they present in
numbers of natural products and biologically active molecules. Herein, a
novel and convenient copper-catalyzed oxidative intramolecular
cyclization of N-(2-acetylphenyl)picolinamide for the synthesis of
2-hydroxy-indolin-3-ones has been developed. Moreover, the detailed
mechanism presented is supported by control experiments and density
function-al theory calculations. This method provides direct access to
2-hydroxy-indolin-3-ones in high yield and good functional group
tolerance. Atom-economy, avoidance of the preparation for substrates and
step economy make this protocol be practical. This strategy provides an
alternative synthetic method to ex-plore the synthetic application of
various types of 2-hydroxy-indolin-3-ones and their enantiopure
deriv-atives.