Polyhydroxylated indolines and oxindoles from C-glycosides via sequential Henry reaction, Michael addition, and reductive amination/amidation.
6-nitro-2'-carbonyl-C-glycofuranosides synthesized via Henry reaction from 1-C-allyl 5-aldo-C-glycoside underwent an intramolecular Michael addition to afford nitrocyclohexanol derivatives in good to excellent yield. Reduction of the nitro group followed by intramolecular amination with ketone and aldehyde and amidation with ester produced indoline and oxindole derivatives, respectively, in excellent yield.
Zou
Wei
W
Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6. wei.zou@nrc-cnrc.gc.ca
Wu
An-Tai
AT
Bhasin
Milan
M
Sandbhor
Mahendra
M
Wu
Shih-Hsiung
SH
D000586:Amination; D006027:Glycosides / Q000737:chemistry*; D006900:Hydroxylation; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000078183:Oxindoles
D006027:Glycosides; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; C057812:indoline