Home / Publications / One-pot synthesis of 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f]-1,3,5-triazepine in ionic liquids

One-pot synthesis of 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f]-1,3,5-triazepine in ionic liquids

Aleksei Borisovich Sheremetev 1
Aleksei Borisovich Sheremetev
, 
Natal'ya Stepanovna Aleksandrova 1
Natal'ya Stepanovna Aleksandrova
, 
Kirill Yu Suponitsky 2
Kirill Yu Suponitsky
, 
Mikhail Yuvenal'evich Antipin 2
Mikhail Yuvenal'evich Antipin
, 
Vladimir Alexandrovich Tartakovsky 1
Vladimir Alexandrovich Tartakovsky
10.1016/j.mencom.2010.09.002
Published 2010-09-09
Communication , Volume 20, Issue 5, 249-252
38
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Sheremetev A. B. et al. One-pot synthesis of 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f]-1,3,5-triazepine in ionic liquids // Mendeleev Communications. 2010. Vol. 20. No. 5. pp. 249-252.
GOST all authors (up to 50) Copy
Sheremetev A. B., Aleksandrova N. S., Suponitsky K. Yu., Antipin M. Y., Tartakovsky V. A. One-pot synthesis of 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f]-1,3,5-triazepine in ionic liquids // Mendeleev Communications. 2010. Vol. 20. No. 5. pp. 249-252.
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TY - JOUR
DO - 10.1016/j.mencom.2010.09.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.09.002
TI - One-pot synthesis of 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f]-1,3,5-triazepine in ionic liquids
T2 - Mendeleev Communications
AU - Sheremetev, Aleksei Borisovich
AU - Aleksandrova, Natal'ya Stepanovna
AU - Suponitsky, Kirill Yu
AU - Antipin, Mikhail Yuvenal'evich
AU - Tartakovsky, Vladimir Alexandrovich
PY - 2010
DA - 2010/09/09
PB - Mendeleev Communications
SP - 249-252
IS - 5
VL - 20
ER -
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@article{2010_Sheremetev,
author = {Aleksei Borisovich Sheremetev and Natal'ya Stepanovna Aleksandrova and Kirill Yu Suponitsky and Mikhail Yuvenal'evich Antipin and Vladimir Alexandrovich Tartakovsky},
title = {One-pot synthesis of 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f]-1,3,5-triazepine in ionic liquids},
journal = {Mendeleev Communications},
year = {2010},
volume = {20},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.09.002},
number = {5},
pages = {249--252},
doi = {10.1016/j.mencom.2010.09.002}
}
MLA
Cite this
MLA Copy
Sheremetev, Aleksei Borisovich, et al. “One-pot synthesis of 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f]-1,3,5-triazepine in ionic liquids.” Mendeleev Communications, vol. 20, no. 5, Sep. 2010, pp. 249-252. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.09.002.

Abstract

Nitration of 3,4-diaminofurazan with HNO3, followed by condensation of the di(nitramine) intermediate with N,N-bis(hydroxymethyl)-N-nitroamine or N,N-bis(acetoxymethyl)-N-nitroamine in ionic liquids affords the title compound in good yield.

References

1.
E. Yu. Orlova, Khimiya i tekhnologiya brizantnykh vzryvchatykh veshchestv (Chemistry and Technology of High Explosives), Khimiya, Leningrad, 1981 (in Russian).
2.
Organic Energetic Compounds, ed. P. L. Marinkas, Nova Science Publ. Inc., New York, 1996.
3.
Energeticheskie kondensirovannye sistemy (Energetic Condensed Systems), 2nd edn., ed. B. P. Zhukov, Yanus-K, Moscow, 2000 (in Russian).
4.
The mechanism of thermal decomposition of secondary nitramines
Shu Y., Korsunskii B.L., Nazin G.M.
Russian Chemical Reviews, 2004
5.
Structure and Bonding: High Energy Density Compounds, ed. T. M. Klapötke, Springer, Berlin, Heidelberg, 2007, vol. 125.
6.
Agrawal J.P., Hodgson R.D.
2006
7.
10.1016/j.mencom.2010.09.002_bib0005_7
Willer
J. Mex. Chem. Soc., 2009
8.
Methods of synthesis and properties of hexanitrohexaazaisowurtzitane
Sysolyatin S.V., Lobanova A.A., Chernikova Y.T., Sakovich G.V.
Russian Chemical Reviews, 2005
9.
Methods for the synthesis of polycyclic nitramines
Sysolyatin S.V., Sakovich G.V., Surmachev V.N.
Russian Chemical Reviews, 2007
10.
Synthesis and chemistry of some furazano- and furoxano[3,4-b]piperazines
Willer R.L., Moore D.W.
Journal of Organic Chemistry, 1985
12.
10.1016/j.mencom.2010.09.002_bib0015_3
Lowe-Ma
Acta Crystallogr., 1990
13.
I. V. Tselinskii, S. F. Mel’nikova, T. V. Romanova, S. V. Pirogov, G. Kh. Khisamutdinov, T. A. Mratkhuzina, V. L. Korolev, I. Z. Kondyukov, I. Sh. Abdrakhmanov and S. P. Smirnov, Zh. Org. Khim., 1997, 33, 1739 (Russ. J. Org. Chem., 1997, 33, 1656).
14.
A. N. Terpigorev and S. B. Rudakov, Zh. Org. Khim., 1998, 34, 1078 (Russ. J. Org. Chem., 1998, 34, 1026).
15.
V. L. Korolev, T. V. Petukhova, T. S. Pivina, A. B. Sheremetev, E. A. Miroshnichenko and V. P. Ivshin, Khim. Geterotsikl. Soedin., 2004, 1817 [Chem. Heterocycl. Compd. (Engl. Transl.), 2004, 40, 1568].
16.
A. B. Sheremetev, Ross. Khim. Zh. (Zh. Ross. Khim. Ob-va im. D. I. Mendeleeva), 1997, 41 (2), 43 [Mendeleev. Chem. J. (Engl. Transl.), 1997, 41 (2), 62].
18.
A. S. Ermakov, S. A. Serkov, V. A. Tartakovskii, T. S. Novikova and L. I. Khmel’nitskii, Khim. Geterotsikl. Soedin., 1994, 1129 [Chem. Heterocycl. Compd. (Engl. Transl.) 1994, 30, 976].
19.
Tetrazolo[1,5-b][1,2,4]triazines: an alternate synthesis and chemistry
Willer R.L., Henry R.A.
Journal of Organic Chemistry, 1988
20.
Retardation of monomolecular reactions in the solid phase
Burov Y.M., Nazin G.M., Manelis G.B.
Russian Chemical Bulletin, 1999
23.
Sheremetev A.B., Yudin I.L.
Mendeleev Communications, 2005
24.
Sheremetev A.B., Aleksandrova N.S., Dmitriev D.E.
Mendeleev Communications, 2006
25.
Sheremetev A.B., Yudin I.L., Suponitsky K.Y.
Mendeleev Communications, 2006
26.
Aliphatic nitramino alcohols and their derivatives
Gafarov A.N., Shakirova G.T.
Russian Chemical Bulletin, 2009
27.
Chemistry of Urea Nitro Derivatives: IV. Reaction of N,N'-Dinitrourea with Formaldehyde
Il'yasov S.G., Lobanova A.A., Popov N.I., Sataev R.R.
Russian Journal of Organic Chemistry, 2002
28.
Denkstein J., Kadeřábek V.
Collection of Czechoslovak Chemical Communications, 2013
29.
Condensations of Primary Aliphatic Nitramines with Formaldehyde
Goodman L.
Journal of the American Chemical Society, 1953
30.
10.1016/j.mencom.2010.09.002_bib0060_2
Ivshin
Zh. Org. Khim., 1981
31.
10.1016/j.mencom.2010.09.002_bib0060_3
Marchenko
Zh. Org. Khim., 1986
32.
Preparation ofN, N-dialkyl methylenebisnitramines
Tartakovskii V.A., Ermakov A.S., Koroban V.A., Alimov F.R., Sigai N.V.
Russian Chemical Bulletin, 1993
33.
Synthesis and properties of methylene-bis-(nitraminofurazans)
Willer R.L., Day R.S., Gilardi R., George C.
Journal of Heterocyclic Chemistry, 1992
34.
Sulfamic acid andN-alkylsulfamates in the synthesis of nitro derivatives of guanidine and aminofurazan
Ermakov A.S., Serkov S.A., Tartakovskii V.A., Novikova T.S., Khmel'nitskii L.I.
Russian Chemical Bulletin, 1995
35.
I. V. Tselinskii, S. F. Mel’nikova and S. N. Vergizov, Zh. Org. Khim., 1995, 31, 1234 (in Russian).
36.
A. Gunasekaran, T. Jayachandran, J. H. Boyer and M. L. Trudell, J. Heterocycl. Chem., 1995, 32, 1405.
37.
Electrooxidation of primary nitramine anions on platinum in MeCN
Frolovskii V.A., Petrosyan V.A.
Russian Chemical Bulletin, 1999
38.
S. D. Shaposhnikov, T. V. Romanova, N. P. Spiridonova, S. F. Mel’nikova and I. V. Tselinskii, Zh. Org. Khim., 2004, 40, 922 (Russ. J. Org. Chem., 2004, 40, 884).
39.
A. V. Sergievskii, T. V. Romanova, S. F. Melnikova and I. V. Tselinskii, Zh. Org. Khim., 2005, 41, 270 (Russ. J. Org. Chem., 2005, 41, 261).
40.
Reactions of 3-amino-4-methylfurazan with nitrating agents
Sheremetev A.B., Aleksandrova N.S.
Russian Chemical Bulletin, 2005
41.
4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data
Suponitsky K.Y., Lyssenko K.A., Antipin M.Y., Aleksandrova N.S., Sheremetev A.B., Novikova T.S.
Russian Chemical Bulletin, 2009
42.
L. A. Aslanova, M. A. Zakharov and N. L. Abramycheva, Ionnie zhidkosti v ryadu rastvoritelei (Ionic Liquids as Solvents), Izd. MGU, Moscow, 2005 (in Russian).
43.
Electrophilic reactions of aromatic and heteroaromatic compounds in ionic liquids
Borodkin G.I., Shubin V.G.
Russian Journal of Organic Chemistry, 2006
46.
Electrophilic Nitration of Aromatics in Ionic Liquid Solvents
Laali K.K., Gettwert V.J.
Journal of Organic Chemistry, 2000
47.
M. J. Earle and S. P. Katdare, US Patent 2004/0024266, 2004.
50.
Novikova T.S., Mel’nikova T.M., Kharitonova O.V., Kulagina V.O., Aleksandrova N.S., Sheremetev A.B., Pivina T.S., Khmel’nitskii L.I., Novikov S.S.
Mendeleev Communications, 1994
51.
R. L. Willer, R. S. Day and D. J. Park, US Patent 5460669, 1995.
52.
The crystal structure of cyclotrimethylenetrinitramine
Choi C.S., Prince E.
Acta Crystallographica Section B, 1972
53.
J. Bernshtein, Polymorphism in Molecular Crystals, Clarendon Press, Oxford, 2002..
54.
The Cambridge Structural Database: a quarter of a million crystal structures and rising
Allen F.H.
Acta Crystallographica Section B Structural Science, 2002
55.
Cambridge Structural Database, 2009, Version 5.30.
57.
A. B. Sheremetev, E. A. Ivanova, N. P. Spiridonova, S. F. Melnikova, I. V. Tselinsky, K. Yu. Suponitsky and M. Yu. Antipin, J. Heterocycl. Chem., 2005, 42, 1237.
58.
10.1016/j.mencom.2010.09.002_bib0120_2
Lowe-Ma
Acta Crystallogr., 1990
59.
Sheremetev A.B., Aleksandrova N.S., Suponitsky K.Y., Antipin M.Y.
Mendeleev Communications, 2009
60.
M. J. Frisch, G.W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. Vreven, Jr., K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K.Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M.W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford CT, 2004.
62.
T. A. Keith, AIMAll (Version 09.04.23), 2009, http://aim.tkgristmill.com.
64.
About the evaluation of the local kinetic, potential and total energy densities in closed-shell interactions
Espinosa E., Alkorta I., Rozas I., Elguero J., Molins E.
Chemical Physics Letters, 2001