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Synthesis 2003(10): 1586-1590
DOI: 10.1055/s-2003-40516
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient and Improved Halogenation of 3,5-Diarylisoxazoles Using N-Halosuccinimides

Ruth Ann Day, Jacqueline A. Blake, Chad E. Stephens*
Center for Biotechnology and Drug Design, Department of Chemistry, Georgia State University, Atlanta, GA 30303
Fax: 404-651-1416; e-Mail: checes@panther.gsu.edu;
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Publikationsverlauf

Received 4 April 2003
Publikationsdatum:
08. Juli 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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23

A volatile pink color developed during the deiodinations which is presumed to be iodine acetate.