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

被引：9

作者：

Shvets, A. O. ^{[1
,2
]}

Konnov, A. A. ^{[1
]}

Klenov, M. S. ^{[1
]}

Churakov, A. M. ^{[1
]}

Strelenko, Yu A. ^{[1
]}

Tartakovsky, V. A. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

[2] Dmitry Mendeleev Univ Chem Technol Russia, 9 Miusskaya Pl, Moscow 125047, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2020年 / 69卷 / 04期

关键词：

1; 2; 3; 4-tetrazine; 3-dioxides; 3-triazoles; furoxans; 3a; 4; 6a-tetraazapentalenes; azides; cyclization; energetic compounds; ISO-DTTO; 1,2,3,4-TETRAZINE;

D O I：

10.1007/s11172-020-2826-3

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 degrees 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 (Delta H degrees(f) = 1005 kJ mol(-1)) and optimal density.

引用

页码：739 / 741

页数：3

共 50 条

[1] Synthesis of 2-(6-nitrobenzofuroxan-4-yl)-2H-[1,2,3]triazolo-[4,5-e][1,2,3,4]tetrazine 4,6-dioxide
A. O. Shvets
A. A. Konnov
M. S. Klenov
A. M. Churakov
Yu. A. Strelenko
V. A. Tartakovsky
Russian Chemical Bulletin, 2020, 69 : 739 - 741
[2] Synthesis and Characterization of Novel 2-(1,2,3-Triazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazoles and 2-(4,5-Dihydro-1H-pyrazol-1-yl)-4-(1H-1,2,3-triazol-4-yl)thiazoles
Kariuki, Benson M.
Abdel-Wahab, Bakr F.
Mohamed, Hanan A.
Bekheit, Mohamed S.
El-Hiti, Gamal A.
MOLECULES, 2022, 27 (24):
[3] Synthesis and antiviral and antitumor activities of 2H-[1,2,3]triazolo[4,5-d]pyrimidines and 1H-, 2H-, and 3H-[1,2,3]triazolo[4,5-d]pyrimidin-5(4H)-one-7(6H)-thiones
Islam, Rafiqul
Nagamatsu, Tomohisa
HETEROCYCLES, 2006, 68 (11) : 2387 - 2402
[4] Synthesis of [1,2,3]triazolo-[4',5':4,5]pyrimido[1,6-a]benzimidazole, a new heterocyclic system
N. T. Pokhodylo
V. S. Matiychuk
M. D. Obushak
Chemistry of Heterocyclic Compounds, 2009, 45 : 245 - 247
[5] Synthesis of thiazolo[4,5-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives
Lee, Hyuck Joo
Kim, Sung Min
Song, Yang-Heon
HETEROCYCLIC COMMUNICATIONS, 2013, 19 (02) : 101 - 104
[6] Synthesis of New Pyrimido[4,5-e][1,2,4] triazolo[3,4-b][1,3,4] thiadiazine Derivatives via S/N Smiles Rearrangement
Ebrahimpour, Zahra
Shiri, Ali
Bakavoli, Mehdi
Seyedi, Seyed Mohammad
Asghari, Tayebe
Mague, Joel
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (01) : 235 - 241
[7] Synthesis of 1,2,3,4-Tetrazine 1,3-Dioxides Annulated with 1,3 a,4,6 a-Tetraazapentalene Systems
Konnov, Alexey A.
Klenov, Michael S.
Churakov, Aleksandr M.
Strelenko, Yurii A.
Dmitrienko, Artem O.
Puntus, Lada N.
Lyssenko, Konstantin A.
Tartakovsky, Vladimir A.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (12) : 2534 - 2543
[8] SYNTHESIS OF [1,2,3]TRIAZOLO[4′,5′:4,5]PYRIMIDO[1,6-a]BENZIMIDAZOLE, A NEW HETEROCYCLIC SYSTEM
Pokhodylo, N. T.
Matiychuk, V. S.
Obushak, M. D.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (02) : 245 - 247
[9] SYNTHESIS OF A NEW HETEROCYCLIC SYSTEM - PYRIDO[3′,2′:4,5]THIENO-[2,3-e][1,2,3]TRIAZOLO[1,5-a]PYRIMIDINE
Pokhodylo, N. T.
Matiychuk, V. S.
Obushak, N. D.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) : 881 - 883
[10] Synthesis of a new heterocyclic system – pyrido[3',2':4,5]thieno- [2,3-e][1,2,3]triazolo[1,5-a]pyrimidine
N. T. Pokhodylo
V. S. Matiychuk
N. D. Obushak
Chemistry of Heterocyclic Compounds, 2009, 45 : 881 - 883

← 1 2 3 4 5 →