Synthesis of tetrafunctionalized 2-azido-3-hydroxy-1,4-diones and their transformation into 5-substituted 3-acylisoxazoles

Éva Juhász-Tótha, Tamás Patonay

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An efficient synthesis of 2-azido-3-hydroxy-1,4-diones, based on the base-induced coupling of α-azido ketones and α-oxo aldehydes, has been developed. The coupling reaction took place with moderate to good diastereoselectivity. The relative configurations of the adducts have been determined by X-ray analysis. Treatment of tetrafunctionalized synthons 2-azido-3-hydroxy-1,4-diones with mesyl chloride in the presence of base afforded 5-substituted 3-acylisoxazoles, through 2-azido-2-alkene-1,4-dione intermediates. Analogous treatment of α-azido ketones with α-oxo esters resulted in the formation of the unstable 3-azido-2-hydroxy-4-oxobut-anoates.

Original languageEnglish
Pages (from-to)3055-3064
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - Sep 2002

Keywords

  • Aldol reaction
  • Azides
  • C-C coupling
  • Diastereoselectivity
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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