42031-70-9Relevant articles and documents
Copper-mediated construction of spirocyclic bis-oxindoles via a double C-H, Ar-H coupling process
Drouhin, Pauline,Hurst, Timothy E.,Whitwood, Adrian C.,Taylor, Richard J.K.
, p. 4900 - 4903 (2014)
A double C-H, Ar-H coupling process for the conversion of bis-anilides into spirocyclic bis-oxindoles, enabling the concomitant formation of two all-carbon quaternary centers at oxindole 3-positions in a diastereoselective manner, is described. The optimum cyclization conditions utilize stoichiometric Cu(OAc)2·H2O/KOtBu in DMF at 110 °C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28-77%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.
Substrate scope in the copper-mediated construction of bis-oxindoles via a double C-H/Ar-H coupling process
Drouhin, Pauline,Hurst, Timothy E.,Whitwood, Adrian C.,Taylor, Richard J.K.
supporting information, p. 7124 - 7136 (2015/03/30)
Abstract The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)2·H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method.
