Synthesis of 3,4,5-trisubstituted isoxazoles via sequential [3 + 2] cycloaddition/silicon-based cross-coupling reactions.
[reaction: see text] A [3 + 2] cycloaddition reaction between alkynyldimethylsilyl ethers and aryl and alkyl nitrile oxides to produce isoxazolylsilanols has been developed. The cross-coupling reactions of these heterocyclic silanols with a variety of aryl iodides affords 3,4,5-trisubstituted isoxazoles. This sequential process allows for rapid variation of substituents at the 3, 4, and 5 positions of the isoxazole.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Kallemeyn
Jeffrey M
JM
D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012825:Silicon / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D007555:Isoxazoles; D012825:Silicon