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Reactions of 1-amino-2-nitroguanidine with glyoxal

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Abstract

The reactions of 1-amino-2-nitroguanidine with glyoxal under conditions of acidic and alkaline catalysis have been comprehensively studied. The obtained glyoxal dihydrazone, 3-nitroamino-1,2,4-triazine sodium salt, 5-hydroxy-4,5-dihydro-3-nitroamino-1,2,4-triazine, and its 5-alkoxy- and 5-aminonitroguanidyl derivatives (products of the reactions with 1-amino-2-nitroguanidine and alcohols) have been characterized by 1H, 13C–{1H} NMR, IR, and UV spectroscopy methods.

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References

  1. Metelkina, E.L., Novikova, N.A., Berdonosova, S.N., and Berdonosov, D.Yu., Russ. J. Org. Chem., 2005, vol. 41, no. 3, p. 440. DOI: 10.1007/s11178-005-0184-0.

    Article  CAS  Google Scholar 

  2. Efimova, T.P., Ozerova, O.Yu., Belik, I.V., Novikova, T.A., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2012, vol. 82, no. 8, p. 1409. DOI: 10.1134/S1070363212080129.

    Article  CAS  Google Scholar 

  3. Efimova, T.P., Ozerova, O.Yu., Novikova, T.A., Baichurin, R.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2014, vol. 84, no. 8, p. 1496. DOI: 10.1134/S1070363214080088.

    Article  CAS  Google Scholar 

  4. Metelkina, E.L., Novikova, N.A., and Telenyuk, S.E., Zh. Org. Khim., 1999, vol. 35, no. 11, p. 1619.

    Google Scholar 

  5. McKay, A.F., Chem. Rev., 1952, vol. 51, no. 2, p. 301. DOI: 10.1021/cr60159a003.

    Article  CAS  Google Scholar 

  6. Zhaohai Q., China Patent 2216324 ?1, 2010.

  7. Metelkina, E.L., Russ. J. Org. Chem., 2008, vol. 44, no. 4, p. 450. DOI: 10.1134/S1070428008040040.

    Article  Google Scholar 

  8. Astrat’ev, A., Dashko, D., and Stepanov, A., New Trends in Research of Energetic Materials, 2011, vol. 2, p. 469.

    Google Scholar 

  9. Mazitova, A.K. and Khamaev, V.Kh., Nesimmetrichnye triaziny. Poluchenie, svoistva i primenenie (Symmetrical Triazines. Preparation, Properties, and Applications), Ufa: GINTL “Reaktiv,” 1999.

    Google Scholar 

  10. Paudler, W.W. and Chen, T.K., J. Heterocycl. Chem., 1970, vol. 7, p. 767. DOI: 10.1002/jhet.5570070403.

    Article  CAS  Google Scholar 

  11. Klemmensen, P., Schroll, G., and Lawesson, S., Ark. Kemi., 1968, vol. 28, p. 405.

    Google Scholar 

  12. Alekseyev, V.V., Saminskaya, A.G., and Yakimovich, S.I., Chem. Heterocycl. Compd., 2012, vol. 48, no. 3, p. 476. DOI: 10.1007/s10593-012-1018-y.

    Article  CAS  Google Scholar 

  13. Zelenin, K.N., Kuznetsova, O.B., and Alekseyev, V.V., Chem. Heterocycl. Compd., 1992, vol. 28, no. 10, p. 1211. DOI: 10.1007/BF00529591.

    Article  Google Scholar 

  14. Rusinov, V.L., Pilicheva, T.L., Chupakhin, O.N., Klyuev, N.A., and Allakhverdieva, D.T., Chem. Heterocycl. Compd., 1986, vol. 22, no. 5, p. 543. DOI: 10.1007/BF00519536.

    Article  Google Scholar 

  15. Attanasi, O.A., de Crescentini, L., Filippone, P., Foresti, E., and Mantellini, F., J. Org. Chem., 2000, vol. 65, no. 9, p. 2820. DOI: 10.1021/jo9917792.

    Article  CAS  Google Scholar 

  16. Metelkina, E.L. and Novikova, N.A., Zh. Org. Khim., 1993, vol. 29, no. 1, p. 2390.

    CAS  Google Scholar 

  17. Morozova, N.S., Metelkina, E.L., Novikova, N.A., Shlyapochnikov, V.A., Sergienko, O.I., and Perekalin, V.V., Zh. Org. Khim., 1983, vol. 19, no. 6, p. 1228.

    CAS  Google Scholar 

  18. Henry, R.A., Makovsky, R.C., and Smith, G.B.L., J. Am. Chem. Soc., 1951, vol. 73, no. 1, p. 474. DOI: 10.1021/ja01145a513.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, nab. reki Moiki 48, St. Petersburg, i]191186, Russia

    O. Yu. Ozerova, T. P. Efimova, T. A. Novikova & V. M. Berestovitskaya

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  1. O. Yu. Ozerova
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  2. T. P. Efimova
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  3. T. A. Novikova
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  4. V. M. Berestovitskaya
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Correspondence to O. Yu. Ozerova.

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Original Russian Text © O.Yu. Ozerova, T.P. Efimova, T.A. Novikova, V.M. Berestovitskaya, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 11, pp. 1842–1850.

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Ozerova, O.Y., Efimova, T.P., Novikova, T.A. et al. Reactions of 1-amino-2-nitroguanidine with glyoxal. Russ J Gen Chem 85, 2583–2591 (2015). https://doi.org/10.1134/S1070363215110134

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  • DOI: https://doi.org/10.1134/S1070363215110134

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