A novel ambident reactivity of azolylacroleins

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Abstract

Reaction of azolylacroleins with phosphoranes bearing a conjugated double bond was found to yield either azolyltrienes in a Wittig reaction, or to undergo cyclization to a dihydrobenzene containing the azole substituent. Transformation with an aza-Wittig reagent gave tetrazolylpyridines. The ambident reactivity was found to be dependent on the substituent of the phosphorane, which was rationalized by ab initio (DFT) calculation of the atomic charges of the reaction centres.

Original languageEnglish
Pages (from-to)4730-4736
Number of pages7
JournalTetrahedron
Volume63
Issue number22
DOIs
Publication statusPublished - May 28 2007

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Keywords

  • Ab initio calculation
  • Azolyltriene
  • Phosphorane
  • Wittig reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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