N -arylated oxathiazinane heterocycles are convenient synthons for 1,3-amino ethers and 1,3-amino thioethers.
Anand H ShindeSomeshwar NagamallaShyam SathyamoorthiPublished in: Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents (2020)
This communication describes a variety of nucleophilic ring openings of N -arylated oxathiazinane heterocycles. We find that this reaction is compatible with phenoxides, naphthoxides, and thiolates and allows for the rapid assembly of N -aryl-amino ethers and N -aryl-amino thioethers. Fourteen examples are shown and a mechanistic pathway is hypothesized.