Skip to main content
SpringerLink
Log in

1,2-Di(4-R-furazan-3-yl)glyoximes: Synthesis by the Reduction of 3,4-Bis(4-R-furazan-3-yl)furoxans and Study of the Reactivity of these Compounds

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reduction of 3,4-bis(4-R-furazan-3-yl)furoxans with hydrazine or hydrogen in the presence of palladium on carbon resulted in opening of the furoxan ring and formation of (Z,E)-dioximes of 1,2-di(4-R-furazan-3-yl)ethane-1,2-diones in high yield. The reactivity of the resultant glyoximes was studied.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. V. G. Andrianov and A. V. Eremeev, Khim. Geterotsikl. Soedin., 1155 (1984). [Chem. Heterocycl. Compd., 20, 937 (1984)].

    Google Scholar 

  2. R. M. Paton, in: A. R. Katritzky, C. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984), p. 393.

    Chapter  Google Scholar 

  3. V. G. Andrianov and A. V. Eremeev, Khim. Geterotsikl. Soedin., 1443 (1990). [Chem. Heterocycl. Compd., 30, 1199 (1990)].

    Google Scholar 

  4. R. M. Paton, in: A. R. Katritzky, C. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry II, Vol. 4, Pergamon Press, Oxford (1996), p. 229.

    Chapter  Google Scholar 

  5. L. I. Khmel'nitskii, S. S. Novikov, and T. I. Godovikova, Chemistry of Furoxans: Structure and Synthesis [in Russian], Nauka, Moscow (1996).

    Google Scholar 

  6. L. I. Khmel'nitskii, S. S. Novikov, and T. I. Godovikova, Chemistry of Furoxans: Reactions and Applications [in Russian], Nauka, Moscow (1996).

    Google Scholar 

  7. A. B. Sheremetev, Rossiisk. Khim. Zh., 43 (1997). [Mendeleev Chem. J., 41, 62 (1997)].

    Google Scholar 

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

    Article  Google Scholar 

  9. A. B. Sheremetev, N. N. Makhova, and W. Friedrichsen, in: Advances in Heterocyclic Chemistry, Vol. 78, Academic Press, New York (2001), p. 65.

    Google Scholar 

  10. A. B. Sheremetev and I. L. Yudin, Usp. Khim., 72, 93 (2003). [Russ. Chem. Rev., 72, 87 (2003)].

    Article  Google Scholar 

  11. G. Nikonov and S. Bobrov, in: A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, and R. J. K. Taylor (editors), Comprehensive Heterocyclic Chemistry III, Vol. 5, Elsevier Science, Amsterdam-London (2008), p. 315.

    Chapter  Google Scholar 

  12. A. V. Sheremetev, E. A. Ivanova, N. P. Spiridonova, S. F. Melnikova, I. V. Tselinsky, K. Yu. Suponitsky, and M. Yu. Antipin, J. Heterocycl. Chem., 42, 1237 (2005).

    Article  CAS  Google Scholar 

  13. Z. Feng-qi, C. Pei, H. Rong-zu, L. Yang, Z. Zhi-zhong, Z. Yan-shui, Y.Xu-wu, G. Yin, G. Sheng-li, and S. Qi-zhen, J. Hazard. Mater., 113, 67 (2004).

    Article  Google Scholar 

  14. W. Jun, D. Haishan, H. Y. Gang, and L. J. Shan, in: Proceedings of the 11 th Seminar: New Trends in Research of Energetic Materials, Pardubice, Czech Republic, April 09–11, 2008, p. 182.

  15. A. A. Astrat'ev, D. V. Dashko, and A. I. Stepanov, Vestn. Kazan. Tekhnol. Univ., No. 21, 35 (2011).

  16. A. A. Astrat'ev, D. V. Dashko, and A. I. Stepanov, Cent. Eur. J. Chem., 10, 1087 (2012).

    Article  Google Scholar 

  17. A. I. Stepanov, A. A. Astrat'ev, D. V. Dashko, N. P. Spiridonova, S. F. Mel'nikova, and I. V. Tselinsky, Izv. Akad. Nauk, Ser. Khim., 1019 (2012). [Russ. Chem. Bull., 61, 1024 (2012)].

    Google Scholar 

  18. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, Toronto (1999), p. 355.

    Book  Google Scholar 

  19. S. R. Sandier and W. Karo, Organic Functional Group Preparations, Academic Press, San Diego (1989), p. 431.

    Google Scholar 

  20. A. I. Mikhaleva, A. B. Zaitsev, and B. A. Trofimov, Usp. Khim., 75, 884 (2006). [Russ. Chem. Rev., 75, 797 (2006)].

    Article  Google Scholar 

  21. H. M. S. Kumar, B. V. S. Reddy, P. T. Reddy, and J. S. Yadav, Synthesis, 586 (1999).

  22. B. Das, P. Madhusudhan, and B. Venkataiah, Synlett, 1569 (1999).

  23. A. I. Bosch, P. de la Cruz, E. Diez-Barra, A. Loupy, and F. Langa, Synlett, 1259 (1995).

  24. C. Ramalingan and Y.-T. Park, J. Org. Chem., 72, 4536 (2007).

    Article  CAS  Google Scholar 

  25. Y. Furuya, K. Ishihara, and H. Yamamoto, J. Am. Chem. Soc., 127, 11240 (2005).

    Article  CAS  Google Scholar 

  26. P. R. Dave, F. Forohar, T. Axenrod, K. K. Das, L. Qi, C. Watnick, and H. Yazdekhasti, J. Org. Chem., 61, 8897 (1996).

    Article  CAS  Google Scholar 

  27. F. P. Ballisteri, E. Barbuzzi, G. A. Tomaselli, and R. M. Toscano, Synlett, 1093 (1996).

  28. S. Sasatani, T. Miyazaki, K. Maruoka, and H. Yamamoto, Tetrahedron Lett., 24, 4711 (1983).

    Article  CAS  Google Scholar 

  29. S. Negi, M. Matsukura, M. Mizuno, K. Miyake, and N. Minami, Synthesis, 991 (1996).

  30. P. A. S. Smith and S. E. Gloyer, J. Org. Chem., 40, 2508 (1975).

    Article  CAS  Google Scholar 

  31. K. Narasaka, Pure Appl. Chem., 75, 19 (2003).

    Article  CAS  Google Scholar 

  32. V. M. Peshkova, V. M. Savostina, and E. K. Ivanova, Oximes [in Russian], Nauka, Moscow (1977).

    Google Scholar 

  33. B.-A. Song, X.-H. Liu, S. Yang, D.-Y. Hu, L.-H. Jin, and Y.-T. Zhang, Chin. J. Org. Chem., 25, 507 (2005).

    CAS  Google Scholar 

  34. G. W. A. Milne, CRC Handbook of Pesticides, CRC Press, Boca Raton (1995).

    Google Scholar 

  35. F. Sevgi and A. D. Bedük, World Appl. Sci. J., 19, 192 (2012).

    CAS  Google Scholar 

  36. J. Kassa, K. Kuca, J. Karasova, and K. Musilek, Mini-Rev. Med. Chem., 8, 1134 (2008).

    Article  CAS  Google Scholar 

  37. E. Ābele and E. Lukevics, Org. Prep. Proced. Int., 32, 235 (2000).

    Article  Google Scholar 

  38. P. V. Anokina, T. V. Romanova, S. F. Mel'nikova, and I. V. Tselinsky, Zh. Org. Khim., 47, 1575 (2011). [Russ. J. Org. Chem., 47, 1606 (2011)].

    Google Scholar 

  39. S. Gao and S. W. Ng, Acta Crystallogr., Sect. E: Struct. Rep. Online, 68, o1573 (2012).

  40. A. A. Astrat'ev, S. F. Mel'nikova, S. A. Dushenok, A. A. Kotomin, D. V. Dashko, A. I. Stepanov, O. F. Yakovleva, A. S. Kozlov, D. A. Barannik, L. A. Loskutova, and I. M. Chernega, International Conference "Shock Waves in Condensed Matter" [in Russian], Kiev, 16–21 September, 2012, Kiev (2012), p. 380.

  41. P. Pagoria, M. Zhang, A. DeHope, G. Lee, A. Mitchell, and P. Leonard, in: Proceedings of the 15 th Seminar on New Trends in Research of Energetic Materials (NTREM), Pardubice, Czech Republic, April 18–20, 2012, p. 54.

  42. T. Pasinszki, B. Havasi, B. Hajgató, and N. P. C. Westwood, J. Phys. Chem. A, 113, 170 (2009).

    Article  CAS  Google Scholar 

  43. T. K. Kim, J. H. Choe, B. W. Lee, and K.-H. Chung, Bull. Korean Chem. Soc., 33, 2765 (2012).

    Article  CAS  Google Scholar 

  44. K. J. Dignam and A. F. Hegarty, J. Chem. Soc., Chem. Commun., 862 (1976).

  45. A. Gunasekaran, T. Jayachandran, J. H. Boyer, and M. L. Trudell, J. Heterocycl. Chem., 32, 1405 (1995).

    Article  CAS  Google Scholar 

  46. Yu. A. Strelenko, O. A. Rakitin, and L. I. Khmel'nitskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1023 (1990). [Bull. Acad. Sci. USSR, Div. Chem. Sci., 39, 912 (1990)].

    Google Scholar 

  47. M. Tanaka, T. Shono, and K. Shinra, Anal. Chim. Acta, 46, 125 (1969).

    Article  CAS  Google Scholar 

  48. S. Kinoshita, H. Wakita, and I. Masuda, Bull. Chem. Soc. Jpn, 59, 653 (1986).

    Article  CAS  Google Scholar 

  49. Y. Gök and H. Kantekin, Chem. Ber., 123, 1479 (1990).

    Article  Google Scholar 

  50. E. Buehler and G. B. Brown, J. Org. Chem., 32, 265 (1967).

    Article  CAS  Google Scholar 

  51. E. Abele, R. Abele, J. Popelis, and E. Lukevics, Org. Prep. Proc. Int., 32, 153 (2000).

    Article  CAS  Google Scholar 

  52. S. Yavuz, H. Ozkan, N. Colak, and Y. Yildirir, Molecules, 16, 6677 (2011).

    Article  CAS  Google Scholar 

  53. D. Kubmarawa, J. T. Barminas, and A. O. C. Aliyu, Arch. Appl. Sci. Res., 3, 126 (2011).

    CAS  Google Scholar 

  54. N. E. Alexandrou and A. G. Varvoglis, Org. Magn. Res., 3, 293 (1971).

    Article  CAS  Google Scholar 

  55. M. Macit, H. Bati, and B. Bati, Synth. React. Inorg. Met.-Org. Chem., 28, 833 (1998).

    Article  CAS  Google Scholar 

  56. P. Walstra, W. P. Trompen, and J. T. Hackman, Rec. Trav. Chim. Pays-Bas, 87, 452 (1968).

    Article  CAS  Google Scholar 

  57. L. I. Khmel'nitskii, V. A. Shlyaposhnikov, N. O. Cherskaya, O. L. Lebedev, L. V. Epishina, and G. V. Korotkova, Izv. Akad. Nauk SSSR, Ser. Khim., 174 (1984). [Bull. Acad. Sci. USSR, Div. Chem. Sci., 33, 155 (1981)].

    Google Scholar 

  58. A. Corsaro, U. Chiacchio, and V. Pistarà, Synthesis, 1903 (2001).

  59. F. P. Invidiata, S. Aiello, G. Furnò, E. Aiello, D. Simoni, and R. Rondanin, J. Heterocycl. Chem., 37, 355 (2000).

    Article  CAS  Google Scholar 

  60. A. Szabó and A. Kovács, J. Mol. Struct., 651–653, 615 (2003).

    Article  Google Scholar 

  61. V. I. Kovalenko, I. V. Vigalok, and G. G. Petrova, Zh. Strukt. Khim., 54 (1992). [J. Struct. Chem., 33, 202 (1992)].

    Google Scholar 

  62. H. Cerecetto, M. González, G. Seoane, C. Stanko, O. E. Piro, and E. Castellano, J. Braz. Chem. Soc., 15, 232 (2004).

    Article  CAS  Google Scholar 

  63. J. Charalambous, G. Soobramanien, A. D. Stylianou, G. Manini, L. Operti, and G. A. Vaglio, Org. Mass Spectrom., 18, 406 (1983).

    Article  CAS  Google Scholar 

  64. I. V. Tselinsky, S. F. Mel'nikova, T. V. Romanova, N. P. Spiridonova, and E. A. Dundukova, Zh. Org. Khim., 1419 (2001). [Russ. J. Org. Chem., 37, 1355 (2001)].

    Google Scholar 

  65. Y.-S. Zhou, B.-Z. Wang, J.-K. Li, C. Zhou, L. Hu, Z.-Q. Chen, and Z. Z. Zhang, Acta Chim. Sin., 69, 1673 (2011).

    CAS  Google Scholar 

  66. A. B. Sheremetev, V. G. Andrianov, E. V. Mantseva, E. V. Shatunova, N. S. Aleksandrova, I. L. Yudin, D. E. Dmitriev, B. B. Averkiev, and M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 569 (2004). [Russ. Chem. Bull., 53, 596 (2004)].

  67. S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, John Wiley & Sons, New York (2001), p. 37.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Special Design and Construction Bureau SDCB “Technolog”, 33-A Sovetskii Ave., Saint Petersburg, 192076, Russia

    A. I. Stepanov, D. V. Dashko & A. A. Astrat’ev

Authors
  1. A. I. Stepanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Dashko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Astrat’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. I. Stepanov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 830–845, May, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Stepanov, A.I., Dashko, D.V. & Astrat’ev, A.A. 1,2-Di(4-R-furazan-3-yl)glyoximes: Synthesis by the Reduction of 3,4-Bis(4-R-furazan-3-yl)furoxans and Study of the Reactivity of these Compounds. Chem Heterocycl Comp 49, 776–790 (2013). https://doi.org/10.1007/s10593-013-1309-y

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1309-y

Keywords

Search

Navigation