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 language | English (US) |
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Pages (from-to) | 1586-1590 |
Number of pages | 5 |
Journal | Synthesis |
Issue number | 10 |
DOIs | |
State | Published - 2003 |
Externally published | Yes |
Keywords
- Halogenation
- Iodo cleavage
- Isoxazoles
- N-halosuccinimides
- Solvent effects
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry