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

Autor: Jean'ne M. Shreeve, Gary L. Gard, Rolf W. Winter, Abe Takashi, Guo-Hong Tao, Young-Hyuk Joo
Rok vydání: 2009
Předmět:
Zdroj: Chemistry - A European Journal. 15:9897-9904
ISSN: 1521-3765
0947-6539
DOI: 10.1002/chem.200901029
Popis: N-C bonded (non-bridged) 5-(1,2,3-triazol-1-yl)tetrazoles were synthesized by the Cu(I)-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 1 in the presence of CuSO(4)5 H(2)O and Na ascorbate at 65-70 degrees C for 48 h in CH(3)CN/H(2)O co-solvent was found to be limited to only terminal alkynes that have electron-withdrawing groups, CF(3)C[triple chemical bond]CH (2 a) and SF(5)C[triple chemical bond]CH (2 b), 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 (3 b) 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 CHCl(3), the click reaction was versatile toward alkynes even those having electron-donating groups. Properties of new products were determined and compared with those of 1. Heats of formation, detonation pressures, detonation velocities and impact sensitivities are reported for these new 5-(1,2,3-triazol-1-yl)tetrazoles.
Databáze: OpenAIRE
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