Formation of Three-membered Nitrogen Heterocycles

Saccharides Containing Aziridine Rings (Epimino Sugars) 

Sugar azides are also important starting-materials for the synthesis of epimino sugars an azido group adjacent to a p-tolylsulfonyloxy group, as in 6 or 8, may be simultaneously reduced and cyclized with Raney nickel to form an aziridine ring, as in 7, especially if the two groups are in the frans-diaxial position.19 22 

An amino aziridine (10) was synthesized23 by direct interaction between hydrazine and a 5,6-dimethane sulfonate (9). 

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