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DOI: 10.1055/s-2007-992419
A Modular Synthesis of Isoxazoles
Contributor(s):Timothy M. Swager, Trisha L. AndrewIowa State University, ames, USA
The Synthesis of Highly Substituted Isoxazoles by Electrophilic Cyclization: An Efficient Synthesis of Valdecoxib
J. Org. Chem. 2007, 72: 9643-9647
Publication History
Publication Date:
23 January 2008 (online)
Key words
isoxazoles - fluorophores - electrophilic cyclization
Significance
A variety of isoxazoles have been synthesized in high yields via an electrophilic cyclization reaction. The iodine handle that is installed as part of the electrocylization is used in a subsequent Suzuki-Miyaura coupling reaction that yields the highly potent COX-2 inhibitor valdecoxib in 74% yield.
Comment
Oxazoles and isoxazoles are stalwart fluorescence standards with long operational lifetimes. Due to their stability, oxazoles are used as scintillation counters in many instruments that emit ionizing radiation. In this paper, the authors present an efficient method to synthesize isoxazoles that will allow for tailoring of the fluorophore’s properties as needed.