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

Research output: Contribution to journalArticle

16 Citations (Scopus)

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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Amination
Addition reactions
Derivatives
Ketones
Aldehydes
Esters
indoline
oxindole
C-glycoside

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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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.",
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Polyhydroxylated indolines and oxindoles from C-glycosides via sequential Henry reaction, Michael addition, and reductive amination/amidation. / Zou, Wei; Wu, An Tai; Bhasin, Milan; Sandbhor, Mahendra; Wu, Shih Hsiung.

In: Journal of Organic Chemistry, Vol. 72, No. 7, 30.03.2007, p. 2686-2689.

Research output: Contribution to journalArticle

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AU - Zou, Wei

AU - Wu, An Tai

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AU - Sandbhor, Mahendra

AU - Wu, Shih Hsiung

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