Synthesis of 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo-[4,5-e][1,2,3,4]tetrazine 4,6-dioxide

Synthesis of 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo-[4,5-e][1,2,3,4]tetrazine 4,6-dioxide Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2020, Volume: 69, Number: 4, Pages: 739-741 Pages count : 3 DOI: 10.1007/s11172-020-2826-3

Authors

Shvets A.O. ^1,2 , Konnov A.A. ² , Klenov M.S. ² , Churakov A.M. ² , Strelenko Yu.A. ² , Tartakovsky V.A. ²

Affiliations

1	Dmitry Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

At heating of 2-(2-azido-3,5-dinitrophenyl)-2H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide in toluene at 110 °C, the azido group interacts mainly with the neighboring nitro group and to a lesser extent with the neighboring 1,2,3-triazole ring, resulting in 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide (2) in 68% yield, as well as 8,10-dinitro-5,11-dehydro-5H,11H-[1,2,3,4]tetrazino[5′,6′:4,5]-[1,2,3]triazolo[2,1-a][1,2,3]benzotriazole 1,3-dioxide and 8,10-dinitro-5,11-dehydro-5H,11H-[1,2,3,4]tetrazino[5′,6′:4,5][1,2,3]triazolo[2,1-a][1,2,3]benzotriazole 2,4-dioxide in 5% yields respectively. Furoxan 2 may be of interest as an energetic compound due to the combination of good thermal stability, positive estimated enthalpy of formation (ΔH°f = 1005 kJ mol−1) and optimal density.

Shvets A.O. , Konnov A.A. , Klenov M.S. , Churakov A.M. , Strelenko Y.A. , Tartakovsky V.A.
Synthesis of 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo-[4,5-e][1,2,3,4]tetrazine 4,6-dioxide
Russian Chemical Bulletin. 2020. V.69. N4. P.739-741. DOI: 10.1007/s11172-020-2826-3 WOS Scopus OpenAlex

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