5-(1,2,3-Triazol-1-yl)tetrazole Derivatives of an Azidotetrazole via Click Chemistry

N-C bonded (non-bridged) 5-(1,2,3-triazol-1-yl)tetrazoles were synthesized by the Cu-1-catalyzed 1,3-dipolar azide-alkyne cycloaddition click reaction using 5-azido-N-(propan-2-ylidene)-1H-tetrazole (1). For example, the click reaction of I in the presence of CuSO4 center dot 5H(2)O and Na ascorbate at 65-70 degrees C for 48 h in CH3CN/H2O co-solvent was found to be limited to only terminal alkynes that have electron-withdrawing groups, CF3C CH (2a) and SF5C CH (2b), giving rise to isopropylidene-[5-(4-trifluoromethyl-1,2,3-triazol-1-yl)tetrazol-1-yl]amine (3 a) and isopropylidene-[5-(4-pentafluorosulfanyl-1,2,3-triazol-1-yl)tetrazol-1-yl]-amine (3b) in 47% and 66% yields, respectively. When carried out under conditions using CuI and 2,6-lutidine as catalysts at 0 degrees C for 13 h in CHCl3, the click reaction was versatile toward alkynes even those having electron-donating groups. Properties of new products were determined and compared with those of L Heats of formation, detonation pressures, detonation velocities and impact sensitivities are reported for these new 5-(1,2,3-triazol-1-yl)tetrazoles.