Syntheses of side-chain fluorinated biologically important imidazoles and indoles

We review in this report the preparation of several side-chain fluorinated analogues of biologically important imidazoles and indoles. The building blocks used should also have applications in other synthetic problems. The addition of “FBr” to vinyl imidazole derivatives was used to prepare β-fluoro- and β,β-difluorohistamine and histidinols, as well as β-fluorourocanic acid. Deoxyfluorination of intermediate acylindoles was used to prepare a series of β,β-difluorotryptamine derivative, including the fluorinated analogue of the important neurotransmitter, serotonin.