The amination of difluoro(diethoxyphosphoryl)acetyl chloride: Facile synthetic route to novel amides containing difluoromethylenephosphonate moiety

A convenient route for the synthesis of novel amides containing at least one β-keto-α,α-difluoromethylenephosphonate group has been elaborated. The procedure requires simple stirring of an amine and difluoro(diethoxyphosphoryl)acetyl chloride in THF in the presence of a catalytic amount of DMAP. A wide range of amines has been accepted, including aliphatic and aromatic diamines, diaminobenzidine or amine derivatives, such as Ciprofloxacin.

Graphical abstractReaction of an amine and difluoro(diethoxyphosphoryl)acetyl chloride in THF, in the presence of a catalytic amount of DMAP leads to formation of β-keto-α,α-difluoromethylenephosphonate.Figure optionsDownload full-size imageDownload as PowerPoint slide