Synthesis of 2-Amino-1,2,3-triazole Derivatives from Vicinal Diazides

Triphenylphosphine reacts with naphthoquinone diazide to form almost quantitatively the phosphorane of a unique 2-amino-1,2,3-triazole derivative. This compound undergoes an aza-Wittig reaction with aldehydes and is readily hydrolyzed to the free 2-amino-1,2,3-triazole. The free amine reacts normally with acids and aldehydes. The 2-amino-1,2,3-triazole system is stable and high melting, and most derivatives give the parent ion as the largest peak in the mass spectrum. The compounds absorb at 300−350 nm with a strong emission in the range 500−700 nm, depending upon the substituents. Cyclic voltammetry shows one reversible, single-electron reduction wave.