Synthesis and transformations of some (heteroaryl)acetylazides, (heteroaryl)methyl isocyanates and alkyl (heteroaryl)methyl carbamates

The synthesis of two complex acetyl azides 6 and 10 having an heteroaryl residue bound to the acetyl group through the ring nitrogen, and their further transformations into the corresponding carbamates 7a-b and 11a-b and isocyanates 16 and 14 are described. Hydrolysis of these products results in the elimination of the substituted methyl group from the heterocyclic residue and formation of 1-unsubstituled heterocycles. A similar transformation was also observed under mass measurement conditions.