Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides

Ruth Ann Day, Jacqueline A. Blake, Chad E. Stephens

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The convenient C-4 halogenation of 3,5-diarylisoxazoles using N-halosuccinimides (NBS, NCS, or NIS) in acetic acid is described. A strong acid catalyst was required for efficient halogenation of some isoxazoles depending on the substituent on the 5-phenyl ring. Finally, the 4-iodoisoxazoles were found to undergo a novel proto-deiodination upon heating in the presence of H2SO4.

Original languageEnglish (US)
Pages (from-to)1586-1590
Number of pages5
JournalSynthesis
Issue number10
DOIs
StatePublished - Jan 1 2003
Externally publishedYes

Fingerprint

Halogenation
Isoxazoles
Acetic acid
Acetic Acid
Heating
Catalysts
Acids

Keywords

  • Halogenation
  • Iodo cleavage
  • Isoxazoles
  • N-halosuccinimides
  • Solvent effects

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides. / Day, Ruth Ann; Blake, Jacqueline A.; Stephens, Chad E.

In: Synthesis, No. 10, 01.01.2003, p. 1586-1590.

Research output: Contribution to journalArticle

Day, Ruth Ann ; Blake, Jacqueline A. ; Stephens, Chad E. / Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides. In: Synthesis. 2003 ; No. 10. pp. 1586-1590.
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