November 3, 2007The Journal of Organic Chemistry185 citationsOpen Access
View Full PaperThe Synthesis of Highly Substituted Isoxazoles by Electrophilic Cyclization: An Efficient Synthesis of Valdecoxib
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Abstract
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.