Preparation of 2-amido substituted furans using the Curtius re-arrangement of furan-2-carbonyl azide

Albert Padwa, Tianhua Wu, Christopher A. Ramsden
2000 ARKIVOC  
Dedicated to Gurnos Jones on the occasion of his 70 th birthday and for his many significant contributions to heterocyclic chemistry (Abstract A series of 2-amido substituted furans were readily prepared from furan-2-carbonyl azide. Heating a sample of the azide in a 2:1-benzene/toluene mixture resulted in a Curtius rearrangement and the in situ generation of furanyl isocyanate. Subsequent treatment of this reactive intermediate with either a Grignard reagent or a higher order cyanocuprate
more » ... r cyanocuprate furnished the desired 2-amido substituted furanyl system.
doi:10.3998/ark.5550190.0001.302 fatcat:b34febwux5dfxd32na3mnfov7a