Synthesis of new 3-(2,2,2-trifluoroethyl)-5-hydroxy-5-(phenylsulfanyl- or phenylsulfonyl-methyl)-1,5-dihydropyrrol-2-ones starting from α,β-unsaturated γ-lactones and primary amines

The paper presents an efficient and straightforward transformation of α,β-unsaturated γ-lactones into 2,2,2-trifluoroethyl substituted γ-lactams, starting from a variety of primary amines. The structures of all new compounds were ascribed using 1D NMR (19F, 1H, 13C), IR, MS. Selected 19F, 13C NMR and IR data of γ-lactams were compared to those of one which was characterized by X-ray diffraction analysis. The possible mechanism for the formation of γ-lactams is also presented.

Figure optionsDownload as PowerPoint slide