Facile and general synthesis of quaternary 3-aminooxindoles.
A novel approach to the valuable quaternary 3-aminooxindole skeleton is reported on the basis of intramolecular arylation of enolates of substituted amino acids. The reaction tolerates dialkyl- and arylalkylamines as well as a range of carbon substituents (primary and secondary alkyl, aryl). The cyclization of N-indolyl-substituted substrates is accompanied by direct C-H arylation of the indole, leading to indolo-fused benzodiazepines.
Marsden
Stephen P
SP
School of Chemistry, University of Leeds, Leeds LS2 9JT, UK. s.p.marsden@leeds.ac.uk
Watson
Emma L
EL
Raw
Steven A
SA
D000588:Amines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles
D000588:Amines; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; C057812:indoline