About thirty NH-1,2,3-triazoles with at least one additional functional group in a side chain at C-4 were prepared from propargyl substrates. These reactions included propargyl azides and their [3,3]-sigmatropic rearrangement to generate short-lived allenyl azides, which cyclized to form triazafulvenes that could be trapped by addition of N-or O-nucleophiles. In most cases, simple substrates and cheap sodium azide were utilized as starting compounds, and the syntheses were performed by using a one-pot procedure without isolation of any dangerous azides. This method to prepare NH-1,2,3-triazoles turned out to be compatible with quite different substitution patterns of the propargyl substrate.

The title compounds, including the parent 3-azido-2H-azirine, were generated by low-temperature photolysis of the corresponding 1,1-diazidoethenes, and characterised not only by trapping reactions, but also by direct detection using NMR and in situ IR spectroscopy.

α-Azido alcohols are generated by treating aldehydes with hydrazoic acid in chloroform. These adducts are transformed into geminal azido-halo compounds through the reaction with phosphorus trichloride or phosphorus tribromide, whereas α-azidoalkyl esters are isolated after interaction with acyl chlorides.