Extending Pummerer reaction chemistry. Application to the oxidative cyclization of indole derivatives.
Treatment of 2-(phenylsulfinyl)indoles bearing a pendant nucleophile at C(3) with Tf(2)O/lutidine triggers a Pummerer-like cyclization to furnish 3,3-spirocyclic-2-(phenylthio)indolenine products, which can, in turn, be hydrolyzed to 3,3-spirocyclic oxindoles. [reaction: see text]
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA. ksf@chem.psu.edu
Vidulova
Daniela Boneva
DB
D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; D012821:Silanes; C030374:indole; D012451:Safrole; C005746:sulfoxide