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Reactions of Thioesters with Organic Azides-A Novel Accesss to Imidates and Thioimidates

Mlostoń G., Romański J., Heimgartner H.

Polish Journal of Chemistry

2001

Vol. 75, nr 7

975-982

The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110_C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the "twofold extrusion" ofN2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.