Preparation of a spiroisoxazolinopiperidinylbenzamide-based scaffold

Kristin A. Milinkevich, Mark J. Kurth

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A route to spiroisoxazolinopiperidinylbenzamides has been developed. N-Boc-4-piperidone underwent a Wittig olefination and Boc-deprotection followed by a nucleophilic substitution reaction with 4-fluoro-3-nitrobenzoic acid to yield the starting scaffold 3 in excellent yields. Diversification of the acid with primary amines, followed nitrile oxide formation in situ (aryl oximes treated with bleach) and subsequent 1,3-dipolar cycloaddition to the exo-methylene moiety delivered the spiroisoxazolinopiperdines. Reduction of the arylnitro group followed by acylation with acid chlorides or reductive amination with aldehydes yielded the spiroisoxazolinopiperidinylbenzamide library.

Original languageEnglish (US)
Pages (from-to)3019-3023
Number of pages5
JournalSynlett
Issue number18
DOIs
StatePublished - 2009

Fingerprint

Scaffolds
Piperidones
Amination
Acylation
Nitriles
Acids
Oximes
Cycloaddition
Aldehydes
Oxides
Amines
Chlorides
Substitution reactions
4-fluoro-3-nitrobenzoic acid

Keywords

  • Cycloaddition
  • Isoxazolines
  • Nitrile oxide
  • Nucleophilic substitution
  • Piperidines

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation of a spiroisoxazolinopiperidinylbenzamide-based scaffold. / Milinkevich, Kristin A.; Kurth, Mark J.

In: Synlett, No. 18, 2009, p. 3019-3023.

Research output: Contribution to journalArticle

Milinkevich, Kristin A. ; Kurth, Mark J. / Preparation of a spiroisoxazolinopiperidinylbenzamide-based scaffold. In: Synlett. 2009 ; No. 18. pp. 3019-3023.
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