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

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 furnished the desired 2-amido substituted furanyl system.