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A new preparative method and some chemical properties of 4-R-furazan-3-carboxylic acid amidrazones

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Chemistry of Heterocyclic Compounds Aims and scope

An alternative method has been developed for the preparation of 4-R-furazan-3-carboxylic acid amidrazones (R = OMe, NH2, substituted amino group) by reductive opening of 1,2,4-oxadiazole ring in 4-R derivatives of (1,2,4-oxadiazol-3-yl)furazans by the action of hydrazine. The starting 1,2,4-oxadiazoles were synthesized from 4-aminofurazan-3-carboxylic acid amidoxime. Some chemical properties of the obtained compounds were studied.

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References

  1. Neilson, D. G.; Roger, R.; Heatlie, J. W. M.; Newlands, L. R. Chem. Rev. 1970, 70, 151.

    Article  CAS  Google Scholar 

  2. Rusanov, A. L. Russ. Chem. Rev. 1974, 43, 795. [Usp. Khim. 1974, 43, 1669.]

  3. Watson, K. M.; Neilson, D. G. In PATAI'S Chemistry of Functional Groups. Amidines and Imidates: Vol. 1; Patai, S., Ed.; John Wiley & Sons, Ltd.: Chichester, 1975, p. 492.

    Google Scholar 

  4. Zelenin, K. N.; Solod, O. V.; Khrustalev, V. A. Chem. Heterocycl. Compd. 1989, 25, 717. [Khim. Geterotsikl. Soedin. 1989, 867.]

  5. Aly, A. A.; Nour-El-Din, A. M. ARKIVOC 2008, (i), 153.

  6. Andrianov, V. G.; Eremeev, A. V. Chem. Heterocycl. Сompd. 1984, 20, 937. [Khim. Geterotsikl. Soedin. 1984, 1155.]

  7. Sliwa, W. Heterocycles, 1984, 22, 1571.

    Article  CAS  Google Scholar 

  8. Paton, R. M. In Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1984, vol. 6, p. 393.

    Chapter  Google Scholar 

  9. Paton, R. M. In Comprehensive Heterocyclic Chemistry-II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, vol. 4, p. 229.

    Chapter  Google Scholar 

  10. Sheremetev, A. B. Russ. Chem. Rev. 1999, 68, 137. [Usp. Khim. 1999, 68, 154.]

  11. Sheremetev, A. B.; Makhova, N. N.; Friedrichsen, W. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed., Academic Press, 2001, vol. 78, p. 65.

  12. Sheremetev, A. B. Mendeleev Chemistry Journal (Zhurnal Ross. Khim. Ob-va im. D. I. Mendeleeva) 1997, 41(2), 43 (1997).

    CAS  Google Scholar 

  13. Astrat'ev, A. A.; Stepanov, A. I.; Dashko, D. V.; Sannikov, V. S. Proceedings of St. Petersburg State Technological Institute (Technical University), 2013, (21), 4.

  14. Mel'nikova, S. F.; Tselinskii, I. V. Proceedings of St. Petersburg State Technological Institute (Technical University) 2013, (21), 25.

  15. Andrianov, V. G.; Eremeev, A. V. Chem. Heterocycl. Сompd. 1994, 608. [Khim. Geterotsikl. Soedin. 1994, 693.]

  16. Tselinskii, I. V.; Mel'nikova, S. F.; Pirogov, S. V.; Sergievskii, A. V. Zh. Org. Khim., 1999, 35, 315.

    Google Scholar 

  17. Godovikova, T. I.; Vorontsova, S. K.; Konyushkin, L. D.; Firgang, S. I.; Rakitin, O. A. Russ. Chem. Bull., Int. Ed. 2009, 58, 406. [Izv. Akad. Nauk, Ser. Khim. 2009, 400.]

  18. Godovikova, T. I.; Vorontsova, S. K.; Konyushkin, L. D.; Firgang, S. I.; Rakitin, O. A. Russ. Chem. Bull., Int. Ed. 2010, 59, 483. [Izv. Akad. Nauk, Ser. Khim. 2010, 473.]

  19. Sergievskii, A. V.; Pirogov, S. V.; Mel'nikova, S. F.; Tselinskii, I. V. Russ. J. Org. Chem. 2001, 37, 717. [Zh. Org. Khim. 2001, 37, 755.]

  20. Godovikova, T. I.; Vorontsova, S. K.; Konyushkin, L. D.; Firgang, S. I.; Rakitin, O. A. Russ. Chem. Bull., Int. Ed. 2008, 57, 2440. [Izv. Akad. Nauk, Ser. Khim. 2008, 2390].

  21. Wang, R.; Guo, Y.; Zeng, Z.; Twamley, B.; Shreeve, J. M. Chem.–Eur. J. 2009, 15, 2625.

    Article  CAS  Google Scholar 

  22. Gao, H.; Shreeve, J. M. Chem. Rev. 2011, 111, 7377.

    Article  CAS  Google Scholar 

  23. Wang, B.; Zhang, G.; Huo, G.; Fan, Y.; Fan, X. Chin. J. Chem. 2011, 29, 919.

    Article  CAS  Google Scholar 

  24. Gao, L.; Yang, H.; Wu, B.; Cheng, G.; Lü, C. Chin. J. Energet. Materials 2013, 21, 226.

    CAS  Google Scholar 

  25. Come, J. H.; Green, J.; Marhefka, C.; Harbeson, S. L.; Eur. Patent 1660467.

  26. Pace, A.; Pierro, P. Org. Biomol. Chem. 2009, 7, 4337.

    Article  CAS  Google Scholar 

  27. Paolini, L.; Cignitti, M. Tertrahedron. 1968, 24, 485.

    Article  Google Scholar 

  28. Ruccia, M.; Vivona, N.; Spinelli, D. In Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J., Eds.; Elsivier: New York, 1981, vol. 29, p. 141.

    Google Scholar 

  29. Tyrkov, A. G. Izv. Vuzov, Khimiya i Khim. Tekhnol. 2003, 46(5), 3.

    CAS  Google Scholar 

  30. Eloy, F. Fortschr. Chem. Forsch. 1965, 4, 807.

    Article  Google Scholar 

  31. Andrianov, V. G.; Eremeev, A. V.; Sheremet, Yu. B. Chem. Heterocycl. Comp. 1988, 6, 707. [Khim. Geterotsikl. Soedin. 1988, 856.]

  32. Buscemi, S.; Pace, A.; Palumbo Piccionello, A.; Pibiri, I.; Vivona, N.; Giorgi, G.; Mazzanti, A.; Spinelli, D. J. Org. Chem. 2006, 1, 8106.

    Article  Google Scholar 

  33. Palumbo Piccionello, A.; Pace, A.; Pibiri, I.; Buscemi, S.; Vivona, N. Tetrahedron 2006, 62, 8792.

    Article  CAS  Google Scholar 

  34. Buscemi, S.; Pace, A.; Pibiri, I.; Vivona, N.; Spinelli, D. J. Org. Chem. 2003, 68, 605.

    Article  CAS  Google Scholar 

  35. Buscemi, S.; Pace, A.; Palumbo Piccionello, A.; Macaluso, G.; Vivona, N.; Spinelli, D.; Giorgi, G. J. Org. Chem. 2005, 70, 3288.

    Article  CAS  Google Scholar 

  36. Palumbo Piccionello, A.; Pace, A.; Buscemi, S.; Vivona, N. ARKIVOC 2009, (vi), 235.

  37. Palumbo Piccionello, A.; Guarcello, A.; Buscemi, S.; Vivona, N.; Pace, A. J. Org. Chem. 2010, 75, 8724.

    Article  CAS  Google Scholar 

  38. Andrianov, V. G.; Eremeev, A. V. Chem. Heterocycl. Compd. 1990, 26, 714. [Khim. Geterotsikl. Soedin. 1990, 853.]

  39. Stepanov, A. I.; Sannikov, V. S.; Dashko, D. V.; Astrat'ev, A. A. Proceedings of St. Petersburg State Technological Institute (Technical University) 2014, (26), 42.

  40. Andrianov, V. G.; Rozhkov, E. N.; Eremeev, A. V. Chem. Heterocycl. Compd. 1994, 30, 470. [Khim. Geterotsikl. Soedin. 1994, 534.]

  41. Stepanov, A. I.; Sannikov, V. S.; Dashko, D. V.; Astrat'ev, A. A. Proceedings of St. Petersburg State Technological Institute (Technical University) 2014, (25), 32.

  42. Ichikawa, T.; Kato, T.; Takenishi, T. J. Heterocycl. Chem. 1965, 2, 253.

    Article  CAS  Google Scholar 

  43. Taylor, E. C.; Beardsley, G. P.; Maki, Y. J. Org. Chem. 1971, 36, 3211.

    Article  CAS  Google Scholar 

  44. Li, H.; Yu, Q.; Wang, B.; Lai, W.; Ge, Z.; Li, Y.; Liu, N. Chin. J. Energet. Mater. 2013, 21, 821.

    CAS  Google Scholar 

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Correspondence to Andrei I. Stepanov or Elena V. Stepanova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(4), 350–360

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Stepanov, A.I., Sannikov, V.S., Dashko, D.V. et al. A new preparative method and some chemical properties of 4-R-furazan-3-carboxylic acid amidrazones. Chem Heterocycl Comp 51, 350–360 (2015). https://doi.org/10.1007/s10593-015-1707-4

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