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Synthesis 2003(10): 1586-1590
DOI: 10.1055/s-2003-40516
DOI: 10.1055/s-2003-40516
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Convenient and Improved Halogenation of 3,5-Diarylisoxazoles Using N-Halosuccinimides
Further Information
Received
4 April 2003
Publication Date:
08 July 2003 (online)
Publication History
Publication Date:
08 July 2003 (online)
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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.
Key words
isoxazoles - halogenation - N-halosuccinimides - iodo cleavage - solvent effects
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References
A volatile pink color developed during the deiodinations which is presumed to be iodine acetate.