N-arylated oxathiazinane heterocycles are convenient synthons for 1,3-amino ethers and 1,3-amino thioethers

Abstract

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.