title: Polyhydroxylated indolines and oxindoles from C-glycosides via sequential Henry reaction, Michael addition, and reductive amination/amidation.
abstract: 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.
authors.affiliation: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6. wei.zou@nrc-cnrc.gc.ca
authors.forename: Wei
authors.initials: W
authors.lastname: Zou
authors.forename: An-Tai
authors.initials: AT
authors.lastname: Wu
authors.forename: Milan
authors.initials: M
authors.lastname: Bhasin
authors.forename: Mahendra
authors.initials: M
authors.lastname: Sandbhor
authors.forename: Shih-Hsiung
authors.initials: SH
authors.lastname: Wu
mesh_terms: 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
chemical_list: D006027:Glycosides; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; C057812:indoline