3,5-Isoxazoles from alpha-bromo-pentafluorophenyl vinylsulfonates: synthesis of sulfonates and sulfonamides.
The regioselective 1,3-dipolar cycloaddition of alpha-bromo-pentafluorophenyl vinylsulfonate with nitrile oxides has been used to rapidly access a range of 3,5-isoxazoles which could be converted directly to their corresponding sulfonamides.
Lee
Chieh Chien
CC
Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, UK WC1H 0AJ.
Fitzmaurice
Richard J
RJ
Caddick
Stephen
S
D007555:Isoxazoles / Q000737:chemistry*; D008872:Microwaves; D009570:Nitriles / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D005464:Fluorobenzenes; D005466:Fluorocarbons
D007555:Isoxazoles; D009570:Nitriles; D013449:Sulfonamides; D013451:Sulfonic Acids; D014753:Vinyl Compounds; C478988:pentafluorophenyl vinylsulfonate; D005464:Fluorobenzenes; D005466:Fluorocarbons