Polyhydroxylated indolines and oxindoles from C-glycosides via sequential Henry reaction, Michael addition, and reductive amination/amidation

Wei Zou, An Tai Wu, Milan Bhasin, Mahendra Sandbhor, Shih Hsiung Wu

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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.

Original languageEnglish
Pages (from-to)2686-2689
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number7
DOIs
Publication statusPublished - 2007 Mar 30

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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