623548-08-3Relevant academic research and scientific papers
The synthesis of highly substituted isoxazoles by electrophilic cyclization: An efficient synthesis of valdecoxib
Waldo, Jesse P.,Larock, Richard C.
, p. 9643 - 9647 (2007)
(Chemical Equation Presented) A large number of functionally substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.
Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides
Day, Ruth Ann,Blake, Jacqueline A.,Stephens, Chad E.
, p. 1586 - 1590 (2007/10/03)
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.
