Reactivity of α-arylidene benzoheteracyclanone dibromides toward azide ion: An effective approach to 3-(α-substituted-benzyl)chromones and -1-thiochromones

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Treatment of dibromides of 3-arylidenechromanones and -1-thiochromanones with sodium azide resulted in the formation of 3-(α-azidobenzyl)chromones and -1-thiochromones whereas dibromides having no antiperiplanar vicinal hydrogen in the ring such as flavanone, 1-thioflavanone and benzosuberone derivatives afforded only the parent enones by bromine elimination. Evidence supported the intermediacy of 3-(α-bromobenzyl)chromones and -1-thiochromones in this reaction. These postulated intermediates were prepared in an independent way and transformed into azides in high yield.

Original languageEnglish
Pages (from-to)2895-2907
Number of pages13
JournalTetrahedron
Volume57
Issue number14
DOIs
Publication statusPublished - Apr 2 2001

    Fingerprint

Keywords

  • Azides
  • Chromones
  • Dehalogenation
  • Elimination reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this