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2013. - V. 27. - N 2(142). - P. 95-101

Ivan Borisovic Kozlov, Gennady Fedorovich Rudakov, Victor Fedorovich Zhilin,

Synthesis and properties of 3,6-bis(5-nitro-3-oxo-2,4-dihydro-1,2,4-triazol-4-yl)-1,2,4,5-tetrazine and its salts

The synthesis and properties of energetic 1,2,4,5-tetrazines obtained from bis-3,6-(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine with 5-nitro-2,4-dihydro-3 H -1,2,4-triazol-3-one in presence of bases were described. The new compounds have been identified by FTIR,

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Синтез и свойства 3,6-бис(5-нитро-3-оксо-2,4-дигидро-1,2,4-триазол-4-ил)-1,2,4,5-тетразина и его солей

References

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  21. 1. Chavez D.E., Hiskey M.A. 1,2,4,5-Tetrazine Based Energetic Materials // J. Energ. Mater. _1999. _17. _P. 357_377.
  22. 2. Chavez D.E., Hiskey M.A., Gilardi R.D. 3,3'-Azobis(6-amino1,2,4,5-tetrazine): a novel high-nitrogen energetic materials // Angew. Chem. Int. Ed. _2000. _V.39, _10. _P. 1791_1793.
  23. 3. Chavez D.E., Hiskey M.A., Naud D.L. Tetrazine Explosives // Propellants Explos. Pyrotech. _2004. _29. _P. 209_215.
  24. 4. Chavez D.E., Tappan B.C., Hiskey M.A., Son S., Harry H., Montoya D., Hagelberg S. New High-Nitrogen Materials Based on Nitroguanyl-Tetrazines: Explosive Properties, Thermal Decomposition and Combustion Studies // Propellants Explos. Pyrotech. _2005. _30. _P. 412_417.
  25. 5. Gao H., Wang R., Twamley B., Hiskey M.A., Shreeve J.M. 3-Amino-6-nitramino-tetrazine (ANAT) _ based energetic salts // Chem. Commun. _2006. _P. 4007_4009.
  26. 6. Duddu R., Dave P.R., Damavarapu R., Surapaneni R., Gilardi R., Parrish D. Synthesis of Azido Heterocycles // Synth. Commun. _2008. _38. _P. 767_774.
  27. 7. Chavez D.E., Parrish D.A. New Heterocycles from Tetrazines and Oxadiazoles // J. Heterocycl. Chem. _2009. _46. _P. 88_90.
  28. 8. Sheremetev A.B., Palysaeva N.V., Struchkova M.I., Suponitsky K.Yu., Antipin M.Yu. Copper-Catalyzed C_N Coupling Reactions of Nitrogen-Rich Compounds _ Reaction of Iodofurazans with s-Tetrazinylamines // Eur. J. Org. Chem. _2012. _P. 2266_2272.
  29. 9. Lee K.-Y., Storm C.B., Hiskey M.A., Coburn M.D. An improved synthesis of 5-amino-3-nitro-1H-1,2,4-triazole (ANTA), a useful intermediate for the preparation of insensitive high explosives // J. Energ. Mater. _1991. _9. _P. 415_428.
  30. 10. Chavez D.E., Gilardi R.D. Synthesis of 3,6-bis(3-azido-1,2,4-triazol-1-yl)-1,2,4,5-tetrazine // J. Energ. Mater. _2009. _27. _P. 110_117.
  31. 11. Amandurdyeva A.D., Saraev V.V., Kuz'mina N.E., Golod E.L. Adamantilazoly: VIII. Kislotno-kataliziruemoe Adamantilirovanie 1,2,4-Triazol-5-onov // ZhOKh. _2004. _T.74, _8. _S. 1377_1382.
  32. 12. Chipen G.I., Bokaldere R.P. Alkilirovanie 5-nitro-1,2,4-triazol-3-ona // KhGS. _1969. _T.5, _1. _S. 159_161.
  33. 13. Kofman T.P., Pevzner M.S., Zhukova L.N., Kravchenko T.A., Frolova G.M. Metilirovanie 3-nitro-1,2,4-triazol-5-ona // ZhOrKh. _1980. _T.16,_2. _S. 420_425.
  34. 14. Bedu E., Benhida R., Devys M., Fourrey J-L. Novel 2_-Deoxycytidine Analogues as pH Independent Substitutes of Protonated Cytosines in Triple Helix Forming Oligonucleotides // Tetrahedron Lett. _1999. _V.40, _5. _P. 835_838.
  35. 15. Kofman T.P., Zhukova L.N., Pevzner M.S. Proizvodnye 3-nitro-1,2,4-triazolona-5 // KhGS. _1981. _T.17, _4. _S. 552_558.
  36. 16. Yavari I., Alizadeh A., Anary-Abbasinejad M. Stable 1,6-diionic phosphorus betaines derived from electron-deficient acetylenic compounds // Phosphorus, Sulfur and Silicon. _2002. _V.177, _10. _P. 2379_2383.
  37. 17. Coburn M.D., Lee K-Y. Picryl derivatives of 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one // J. Heterocycl. Chem. _1990. _V.27, _3. _P. 575_577.
  38. 18. Rusinov G.L., Latosh N.I., Ganebnykh I.N., Ishmetova R.I., Ignatenko N.K., Chupakhin O.N. Sintez simmetrichno i nesimmetrichno 3,6-dizameshchennykh N-nukleofilami 1,2,4,5-tetrazinov // ZhOrkh. _2006. _T.42, _5. _S. 772_780.
  39. 19. Lee K.-Y., Stinecipher M.M. Synthesis and Initial Characterisation of Amine Salts of 3-Nitro-l,2,4-triazol-5-one // Propellants Explos. Pyrotech. _1989. _14. _P. 241_244.
  40. 20. Jian-hua Yi, Feng-qi Zhao, Hong-xu Gao, Si-yu Xu, Min-chang Wang, Rong-zu Hu Preparation, characterization, non-isothermal reaction kinetics, thermodynamic properties, and safety performances of high nitrogen compound: Hydrazine 3-nitro-1,2,4-triazol-5-one complex // J. Hazard. Mater. _ 2008. _153. _P. 261_268.

Keywords

1   2   4   4-dihydro-3H-1   4-triazol-3-one   4-дигидро-3H-1   4-триазол-3-он   5-nitro-2   5-tetrazine   5-нитро-2   5-тетразин   energetic salts   nucleophilic substitution   нуклеофильное замещение   энергоемкие соли  


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