SYNTHESIS OF GLYCOAMIDINES USING A MERCURY-PROMOTED REACTION

Glycoamidines are readily prepared by a mercury-promoted reaction of the corresponding thioamides with amines. The reaction appears to involve the participation of bidentate mercury complexes with N-monosubstituted thioamides, whereas N,N-disubstituted derivatives form presumably monocoordinated species. In the light of these assumptions, two different mechanistic pathways can be applicable depending on the starting thioamide. In addition, this protocol enhances the versatility of transformations of organosulfur compounds in the presence of transition metal ions and illustrates novel features.