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Synthesis and Characterization of Bisnitrofurazanofuroxan

  • Lim, Choong-Hwan (High Energy Material Research Center, Department of Chemistry, Inha University) ;
  • Kim, Tae-Keun (High Energy Material Research Center, Department of Chemistry, Inha University) ;
  • Kim, Kyung-Ho (High Energy Material Research Center, Department of Chemistry, Inha University) ;
  • Chung, Kyoo-Hyun (High Energy Material Research Center, Department of Chemistry, Inha University) ;
  • Kim, Jin-Seuk (Agency for Defense Development)
  • Received : 2009.12.29
  • Accepted : 2010.03.13
  • Published : 2010.05.20
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References

  1. Lim, C. H.; Hong, S.; Chung, K.-H.; Kim, J. S.; Cho, J. R. Bull. Korean Chem. Soc. 2008, 29, 1415. https://doi.org/10.5012/bkcs.2008.29.7.1415
  2. Katrizky, A. R.; Sommen, G. L.; Gromova, A. V.; Witek, R. M.; Steel, P. J.; Damavarapu, R. Chem. Heterocycl. Comp. 2005, 41, 111. https://doi.org/10.1007/s10593-005-0116-5
  3. Latypov, N. V.; Bergman, J.; Langlet, A.; Wellmar, U.; Bemm, U. Tetrahedron 1998, 54, 11525. https://doi.org/10.1016/S0040-4020(98)00673-5
  4. Coburn, M. D. J. Heterocycl. Chem. 1968, 5, 83. https://doi.org/10.1002/jhet.5570050114
  5. Aleksandrova, N. S.; Kharitonova, O. V.; Khmelnitskii, L. I.; Kulagina, V. O.; Melnikova, T. M.; Novikov, S. S.; Novikova, T. S.; Pivina, T. S.; Sheremetev, A. B. Mendeleev Commun. 1994, 230.
  6. Agrawal, J. P.; Hodgson, R. D. Organic Chemistry of Explosives; John Wiley & Sons: West Sussex, England, 2007; p 302.
  7. Bohn, H.; Brendel, J.; Martorana, P. A.; Schonafinger, K. Brit. J. Pharm. 1995, 114, 1605. https://doi.org/10.1111/j.1476-5381.1995.tb14946.x
  8. Gasco, A.; Fruttero, R.; Sorba, G. IL Pharmaco 1996, 51, 617.
  9. Cerecetto, H.; Di Maio, R.; Gonzalez, M.; Risso, M.; Saenz, P.; Seoane, G.; Denicola, A.; Peluffo, G.; Quijano, C.; OleaAzar, C. J. Med. Chem. 1999, 42, 1941. https://doi.org/10.1021/jm9805790
  10. Boschi, D.; Cena, C.; Di Stilo, A.; Fruttero, R.; Gasco, A. Bioorg. Med. Chem. 2000, 8, 1727. https://doi.org/10.1016/S0968-0896(00)00098-5
  11. Li, M.; Sishen, F.; Mei, L. G. Chem. Pharm. Bull. 2000, 48, 808. https://doi.org/10.1248/cpb.48.808
  12. Norris, W. P.; Spear, R. J. Propell. Explos. Pyrotech. 1983, 8, 85. https://doi.org/10.1002/prep.830080308
  13. Agrawal, J. P.; Mehilal, R. B. S.; Shinde, P. D. Propell. Explos. Pyrotech. 2003, 28, 77. https://doi.org/10.1002/prep.200390012
  14. Sheremetev, A. B.; Ivanova, E. A.; Spiridonova, N. P.; Tselinsky, I. V.; Suponitsky, K. Y.; Antipin, M. J. Heterocycl. Chem. 2005, 42, 1237. https://doi.org/10.1002/jhet.5570420634
  15. Zhao, F.-Q.; Chen, P.; Hu, R.-Z.; Luo, Y.; Zhang, Z.-Z.; Zhou, Y.-S.; Yang, X.-W.; Gao, Y.; Gao, S.-L.; Shi, Q.-Z. J. Hazardous Materials A 2004, 113, 67. https://doi.org/10.1016/j.jhazmat.2004.07.009
  16. Ichikawa, T.; Kato, T.; Takenishi, T. J. Heterocycl. Chem. 1965, 2, 253. https://doi.org/10.1002/jhet.5570020307
  17. Beaudegnies, R.; Wendeborn, S. Heterocycles 2003, 60, 2417. https://doi.org/10.3987/COM-03-9833
  18. Andranov, V.; Eremeev, A. Khimiya Geterotsiklicheskikh Soedinenii 1994, 3, 420. CAN 123:198702.
  19. Tselinskii, I. V.; Mel’nikova, S. F.; Romanova, T. V.; Spiridonova, N. P.; Dundukova, E. A. Russ. J. Org. Chem. 2001, 37, 1355. https://doi.org/10.1023/A:1013168629562
  20. Wang, J.; Li, J.; Liang, Q.; Huang, Y.; Dong, H. Propel. Explos. Pyrotech. 2008, 33, 347. https://doi.org/10.1002/prep.200800225
  21. Wang, J.; Dong, H.-S.; Huang, Y.-G.; Zhou, X.-Q.; Li, J.-S. Chin. J. Synth. Chem. 2006, 14, 131. CAN 145; 251737.
  22. Lee, S. H.; Jo, I.; Lee, J. H.; Hwang, K.-J. Bull. Korean Chem. Soc. 1997, 18, 1115.
  23. Yu, Z.-X.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 15240.
  24. Matt, C.; Gissot, A.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 2000, 41, 1191. https://doi.org/10.1016/S0040-4039(99)02278-9
  25. Kim, G. Y.; Kim, J.; Lee, J. H.; Kim, H. J.; Hwang, K-J. Bull. Korean Chem. Soc. 2009, 30, 459. https://doi.org/10.5012/bkcs.2009.30.2.459
  26. Boldyrev, M. D.; Gidaspov, B. V.; Nikolaev, V. D.; Soludyuk, G. D. J. Org. Chem. (USSR) 1981, 17, 756.
  27. Lee, G. S.; Mitchell, A. R.; Pagoria, P. F.; Schmidt, R. D. J. Heterocycl. Chem. 2001, 38, 1227. https://doi.org/10.1002/jhet.5570380533
  28. Zhao, F.-Q.; Guo, P.-J.; Hu, R.-Z.; Zhang, H.; Xia, Z.-M.; Gao, H.-X.; Chen, P.; Luo, Y.; Zhang, Z. Z.; Zhuo, Y.-S.; Zhau, H.-A.; Gao, S.-L.; Shi, Q.-Z.; Lu, G.-E.; Jiang, J.-Y. Chin. J. Chem. 2006, 24, 631. https://doi.org/10.1002/cjoc.200690121

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