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Synfacts 2006(3): 0206-0206  
DOI: 10.1055/s-2006-931965
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Tetraazapentalenes: Formation and Rearrangement

Contributor(s): Victor Snieckus, Oleg M. Demchuk
M. H. V. Huynh*, M. A. Hiskey*, D. E. Chavez, R. D. Gilardi
Los Alamos National Laboratory and Naval Research Laboratory, Washington, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

An efficient synthesis of heteroring-annulated tetraazapentalenes 1 by a nucleophilic substitution-reductive cyclization of benztriazole and 2-chloro-3-nitropyridine is reported. Thermolysis of product 1 leads to the interesting but known (F. B. Mallory, P. A. S. Smith, J. H. Boyer Org. Synth. Coll. Vol. IV, 1963, 74-78) formation of an oxadiazole 2 which undergoes a further interesting oxadiazole rearrangement-fragmentation to give the complex heterocycle 3. All compounds were fully characterized (including X-ray crystal structure analysis) and show interesting physicochemical properties such as high explosive performance and yet notable thermal stability.