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A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines

Aleksei Borisovich Sheremetev 1
Aleksei Borisovich Sheremetev
, 
Nadezhda Vladimirovna Palysaeva 1
Nadezhda Vladimirovna Palysaeva
, 
Marina Ivanovna Struchkova 1
Marina Ivanovna Struchkova
, 
Kirill Yu Suponitsky 2
Kirill Yu Suponitsky
10.1016/j.mencom.2012.11.007
Published 2012-11-07
Communication , Volume 22, Issue 6, 302-304
27
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Sheremetev A. B. et al. A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines // Mendeleev Communications. 2012. Vol. 22. No. 6. pp. 302-304.
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Sheremetev A. B., Palysaeva N. V., Struchkova M. I., Suponitsky K. Yu. A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines // Mendeleev Communications. 2012. Vol. 22. No. 6. pp. 302-304.
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TY - JOUR
DO - 10.1016/j.mencom.2012.11.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.007
TI - A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines
T2 - Mendeleev Communications
AU - Sheremetev, Aleksei Borisovich
AU - Palysaeva, Nadezhda Vladimirovna
AU - Struchkova, Marina Ivanovna
AU - Suponitsky, Kirill Yu
PY - 2012
DA - 2012/11/07
PB - Mendeleev Communications
SP - 302-304
IS - 6
VL - 22
ER -
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@article{2012_Sheremetev,
author = {Aleksei Borisovich Sheremetev and Nadezhda Vladimirovna Palysaeva and Marina Ivanovna Struchkova and Kirill Yu Suponitsky},
title = {A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.007},
number = {6},
pages = {302--304},
doi = {10.1016/j.mencom.2012.11.007}
}
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Cite this
MLA Copy
Sheremetev, Aleksei Borisovich, et al. “A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines.” Mendeleev Communications, vol. 22, no. 6, Nov. 2012, pp. 302-304. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.007.

Abstract

3,6-Bis(3,5-dimethylpyrazol-1-yl)-s-tetrazine reacts with weakly based hetarylamines such as aminofurazans, aminoimidazoles, aminotriazoles, aminotetrazoles, or aminotetrazines on heating in MeCN in the presence of M2CO3 (M = K, Cs) to afford 3-hetaryl- amino-s-tetrazines, the products of 3,5-dimethylpyrazolyl group displacement.

References

1.
(a) S. A. Shevelev and I. L. Dalinger, Zh. Org. Khim., 1998, 34, 1127 (Russ. J. Org. Chem., 1998, 34, 1071)
2.
Dinitropyrazoles
Zaitsev A.A., Dalinger I.L., Shevelev S.A.
Russian Chemical Reviews, 2009
3.
(a) Y. Ou, B. Chen, J. Li, S. Dong, J. Li and H. Jia, Heterocycles, 1994, 38, 1651
4.
(b) M. S. Pevzner, Ross. Khim. Zh. (Zh. Ross. Khim. Ob-va im. D. I. Mendeleeva), 1997, 41 (2), 73 [Mendeleev Chem. J. (Engl. Transl.), 1997, 41 (2), 113]
5.
(c) V. A. Ostrovskii, M.S. Pevzner, T.P. Kofman, M.B. Shcherbinin and I. V. Tselinskii, Targets Heterocycl. Syst., 1999, 3, 467
6.
5-Amino-3-nitro-1,2,4-triazole and Its Derivatives
Kofman T.P.
Russian Journal of Organic Chemistry, 2002
7.
Azole-Based Energetic Salts
Gao H., Shreeve J.M.
Chemical Reviews, 2011
8.
(a) V. A. Ostrovskii and G. I. Koldobskii, Ross. Khim. Zh. (Zh. Ross. Khim. Ob-va im. D. I. Mendeleeva), 1997, 41 (2), 84 [Mendeleev Chem. J. (Engl. Transl.), 1997, 41 (2), 133]
9.
(b) T. M. Klapotke, in High Energy Density Materials, ed. T. M. Klapotke, Springer, Berlin, 2007, p. 85
10.
Tetrazoles
Ostrovskii V.A., Koldobskii G.I., Trifonov R.E.
2008
11.
(a) 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]
13.
Monocyclic furazans and furoxans
Sheremetev A.B., Makhova N.N., Friedrichsen W.
Advances in Heterocyclic Chemistry, 2001
15.
1,2,5-Oxadiazoles
Nikonov G., Bobrov S.
2008
16.
Nitro derivatives of 1,3,5-triazine: synthesis and properties
Shastin A.V., Godovikova T.I., Korsunskii B.L.
Russian Chemical Reviews, 2003
17.
Tetrazine Explosives
Chavez D., Hiskey M., Naud D.
Propellants, Explosives, Pyrotechnics, 2004
19.
(c) J. Wang, S. Liang, C. Tian and Y. Wang, Chem. Propellants Polym. Mater., 2011, 9 (4), 91.
20.
(a) D. B. Lempert, G.N. Nechiporenko and S. I. Soglasnova, Fiz. Goren. Vzryva, 2009, 45 (2), 58 (Combust. Explos. Shock Waves, 2009, 45, 160); (b) V. V. Semenov, S.A. Shevelev, A.B. Bruskin, M.I. Kanishchev and A. T. Baryshnikov, Izv. Akad. Nauk, Ser. Khim., 2009, 2014 (Russ. Chem. Bull., Int. Ed., 2009, 58, 2077); (c) T. V. Romanova, M.P. Zelenov, S.F. Mel’nikova and I. V. Tselinsky, Izv. Akad. Nauk, Ser. Khim., 2009, 2123 (Russ. Chem. Bull., Int. Ed., 2009, 58, 2188); (d) K. Yu. Suponitsky, K.A. Lyssenko, M. Yu. Antipin, N.S. Aleksandrova, A.B. Sheremetev and T. S. Novikova, Izv. Akad. Nauk, Ser. Khim., 2009, 2065 (Russ. Chem. Bull., Int. Ed., 2009, 58, 2129); (e) O. P. Shitov, V.L. Korolev and V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2009, 2275 (Russ. Chem. Bull., Int. Ed., 2009, 58, 2347); (f) I. V. Tselinskii, V.V. Tolstyakov, S.M. Putis and S. F. Mel’nikova, Izv. Akad. Nauk, Ser. Khim., 2009, 2283 (Russ. Chem. Bull., Int. Ed., 2009, 58, 2356).
21.
(a) A. Saikia, R. Sivabalan, B.G. Polke, G.M. Gore, A. Singh, A.S. Rao and A. K. Sikder, J. Hazard. Mater., 2009, 170, 306; (b) V. N. Kizhnyaev, F.A. Pokatilov, L.I. Vereshchagin, O.N. Verkhozina, T.L. Petrova, A.G. Prodaikov, G.V. Ratovskii and O. V. Tyukalova, Zh. Prikl. Khim., 2009, 82, 1616 (Russ. J. Appl. Chem., 2009, 82, 1769); (c) P. W. Leonard, C.J. Pollard, D.E. Chavez, B.M. Rice and D. A. Parrish, Synlett, 2011, 2097; (d) T. K. Kim, B.W. Lee and K.-H. Chung, Bull. Korean Chem. Soc., 2011, 32, 3802; (e) A. B. Sheremetev, I.L. Yudin, N.V. Palysaeva and K. Yu. Suponitsky, J. Heterocycl. Chem., 2012, 49, 394; (f) Z. Fu, C. He and F.-X. Chen, J. Mater. Chem., 2012, 22, 60.
22.
New heterocycles from tetrazines and oxadiazoles
Chavez D.E., Parrish D.A.
Journal of Heterocyclic Chemistry, 2009
23.
Sheremetev A.B., Palysaeva N.V., Struchkova M.I.
Mendeleev Communications, 2010
24.
Copper-Catalyzed C-N Coupling Reactions of Nitrogen-Rich Compounds - Reaction of Iodofurazans with s-Tetrazinylamines
Sheremetev A.B., Palysaeva N.V., Struchkova M.I., Suponitsky K.Y., Antipin M.Y.
European Journal of Organic Chemistry, 2012
25.
The first general synthesis of 3-iodo-4-R-furazans
Sheremetev A.B., Shamshina J.L., Dmitriev D.E., Lyubetskii D.V., Antipin M.Y.
Heteroatom Chemistry, 2004
26.
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
27.
(a) M. D. Coburn, G.A. Buntain, B.W. Harris, M.A. Hiskey, K.-Y. Lee and D. G. Ott, J. Heterocycl. Chem., 1991, 28, 2049; (b) D. E. Chavez and M. A. Hiskey, J. Heterocycl. Chem., 1998, 35, 1329; (c) N. I. Latosh, G.L. Rusinov, I.N. Ganebnykh and O. N. Chupakhin, Zh. Org. Khim., 1999, 35, 1392 (Russ. J. Org. Chem., 1999, 35, 1363); (d) G. L. Rusinov, I.N. Ganebnykh and O. N. Chupakhin, Zh. Org. Khim., 1999, 35, 1379 (Russ. J. Org. Chem., 1999, 35, 1350); (e) Z. Novak, B. Bostai, M. Csekei, K. Lorincz and A. Kotschy, Heterocycles, 2003, 60, 2653; (f) S. G. Tolshchina, A.G. Vyakhireva, N.K. Ignatenko, R.I. Ishmetova, I.N. Ganebnykh, P.A. Slepukhin and G. L. Rusinov, Izv. Akad. Nauk, Ser. Khim., 2009, 1245 (Russ. Chem. Bull., Int. Ed., 2009, 58, 1281); (g) S. G. Tolshchina, N.K. Ignatenko, P.A. Slepukhin, R.I. Ishmetova and G. L. Rusinov, Khim. Geterotsikl. Soedin., 2010, 860 [Chem. Heterocycl. Compd. (Engl. Transl.), 2010, 46, 691].
28.
Synthesis of [1,2,4]triazolo[4,3-b]-s-tetrazines with incorporated furazan ring
Sheremetev A.B., Palysaeva N.V., Suponitskii K.Y., Struchkova M.I.
Russian Chemical Bulletin, 2012
29.
I. V. Tselinskii, S.F. Mel’nikova and S. N. Vergizov, Khim. Geterotsikl. Soedin., 1981, 321 [Chem. Heterocycl. Compd. (Engl. Transl.), 1981, 17, 228].
30.
Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds
Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., Taylor R.
Journal of the Chemical Society Perkin Transactions 2, 1987