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5‐(1,2,3‐Triazol‐1‐yl)tetrazole Derivatives of an Azidotetrazole via Click Chemistry
Author(s) -
Abe Takashi,
Tao GuoHong,
Joo YoungHyuk,
Winter Rolf W.,
Gard Gary L.,
Shreeve Jean'ne M.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901029
Subject(s) - tetrazole , chemistry , cycloaddition , triple bond , click chemistry , azide , medicinal chemistry , alkyne , polar effect , amine gas treating , trifluoromethyl , catalysis , organic chemistry , double bond , alkyl
NC 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)‐1 H ‐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 °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 CCH ( 2 a ) and SF 5 CCH ( 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 °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.