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

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

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

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Shreeve, Jean'ne M. Winter, Rolf W. Tao, Guo-hong Gard, Gary L. Abe, Takashi Joo, Young-hyuk
Description	Author Affiliation: Abe T ( Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA.)
Abstract	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)-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 °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.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	38
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-09-28
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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