Skip to main content
SpringerLink
Log in

Synthesis of secondary and tertiary aminofurazans

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Reactions of nitrofurazans with primary and secondary amines were studied. Conditions were found which allow the efficient replacement of the nitro group with these nucleophiles. Transformations of the amidoxime fragment, which is bound to the furazan ring and contains an amino substituent, enable one to substantially expand the spectrum of polyfunctional derivatives. The structures of the amines synthesized were studied by X-ray diffraction analysis.

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

Similar content being viewed by others

References

  1. S. E. Berezina, L. A. Remizova, D. Dielimoriba, and I. N. Domnin, Zh. Org. Khim., 2001, 37, 1700 [Russ. J. Org. Chem., 2001, 37 (Engl. Transl.)].

    Google Scholar 

  2. V. G. Andrianov and A. V. Eremeev, Khim. Geterotsikl. Soedin., 1984, 1155 [Chem. Heterocycl. Compd., 1984 (Engl. Transl.)].

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

  4. A. B. Sheremetev, N. N. Makhova, and W. Friedrichsen, Adv. Heterocycl. Chem., 2001, 78, 65.

    Google Scholar 

  5. A. B. Sheremetev, V. O. Kulagina, I. A. Kryazhevskikh, and T. M. Mel'nikova, Izv. Akad. Nauk, Ser. Khim., 2002, 1411 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1533].

  6. T. I. Godovikova, O. A. Rakitin, S. P. Golova, S. A. Vozchikova, M. V. Povorin, and L. I. Khmel'nitskii, Khim. Geterotsikl. Soedin., 1994, 529 [Chem. Heterocycl. Compd., 1994 (Engl. Transl.)].

  7. T. I. Godovikova, S. P. Golova, S. A. Vozchikova, E. L. Ignat'eva, M. V. Povorin, V. S. Kuz'min, and L. I. Khmel'nitskii, Mendeleev Commun., 1995, 194.

  8. T. I. Godovikova, S. P. Golova, S. A. Vozchikova, E. L. Ignat'eva, M. V. Povorin, and L. I. Khmel'nitskii, Khim. Geterotsikl. Soedin., 1996, 675 [Chem. Heterocycl. Compd., 1996, 32, 580 (Engl. Transl.)].

  9. V. G. Andrianov, V. G. Semenikhina, and A. V. Eremeev, Zh. Org. Khim., 1993, 29, 1062 [Russ. J. Org. Chem., 1993, 29 (Engl. Transl.)].

    Google Scholar 

  10. I. V. Tselinskii, S. F. Mel'nikova, and T. V. Romanova, Zh. Org. Khim., 2001, 37, 1708 [Russ. J. Org. Chem., 2001, 37 (Engl. Transl.)].

    Google Scholar 

  11. V. G. Andrianov, V. G. Semenikhina, and A. V. Eremeev, Khim. Geterotsikl. Soedin., 1992, 687 [Chem. Heterocycl. Compd., 1992 (Engl. Transl.)].

  12. A. B. Sheremetev, O. V. Kharitonova, E. V. Mantseva, V. O. Kulagina, E. V. Shatunova, N. S. Aleksandrova, T. M. Mel'nikova, E. A. Ivanova, D. E. Dmitriev, V. A. Eman, I. L. Yudin, V. S. Kuz'min, Yu. A. Strelenko, T. S. Novikova, O. V. Lebedev, and L. I. Khmel'nitskii, Zh. Org. Khim., 1999, 35, 1555 [Russ. J. Org. Chem., 1999, 35, 1525 (Engl. Transl.)].

  13. Yu. A. Strelenko, A. B. Sheremetev, and L. I. Khmel'nitskii, Khim. Geterotsikl. Soedin., 1992, 1101 [Chem. Heterocycl. Compd., 1992, 927 (Engl. Transl.)].

  14. D. E. Dmitriev, Yu. A. Strelenko, and A. B. Sheremetev, Izv. Akad. Nauk, Ser. Khim., 2002, 277 [Russ. Chem. Bull., Int. Ed., 2002, 51, 290].

  15. A. B. Sheremetev, S. M. Konkina, I. L. Yudin, D. E. Dmitriev, B. B. Averkiev, and M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim.,2003, 1337 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1413].

  16. B. M. Lynch, Can. J. Chem., 1977, 55, 541.

    Google Scholar 

  17. Accurate Molecular Structures: Their Determination and Im-portance (International Union of Crystallography Book Series, Monograph, No. 1), Eds. A. Domenicano and I. Hargittai, Oxford University Press, Oxford, 1992.

    Google Scholar 

  18. A. S. Batsanov and Yu. T. Struchkov, Zh. Strukt. Khim., 1985, 26, 65 [J. Struct. Chem. (USSR), 1985, 26 (Engl. Transl.)].

  19. B. B. Averkiev, M. Yu. Antipin, A. B. Sheremetev, and T. V. Timofeeva, Acta Crystallogr., Sect. C, 2003, 59, 383.

    Google Scholar 

  20. T. S. Novikova, T. M. Melnikova, O. V. Kharitonova, V. O. Kulagina, N. S. Aleksandrova, A. B. Sheremetev, T. S. Pivina, L. I. Khmelnitskii, and S. S. Novikov, Mendeleev Commun., 1994, 138.

  21. G. M. Sheldrick, SHELXTL-97, Version 5.10, Bruker AXS Inc., Madison (WI-53719, USA), 1997.

    Google Scholar 

  22. A. N. Kost, L. G. Yudin, Yu. A. Berlin, and A. P. Terent'ev, Zh. Obshch. Khim., 1959, 29, 3820 [J. Gen. Chem. USSR, 1959, 29 (Engl. Transl.)].

    Google Scholar 

  23. USSR Inventor's Certificate No. 1599372, 1990; Byul. Izobr., 1990, 38, 99 (in Russian); Chem. Abstr., 1991, 114, 185512.

  24. L. Wolff, Chem. Ber., 1895, 28, 69.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. B. Sheremetev, E. V. Mantseva, E. V. Shatunova, N. S. Aleksandrova, I. L. Yudin & D. E. Dmitriev

  2. Latvian Institute of Organic Synthesis, Latvian Academy of Sciences, 21 str. Aizkraukles, 226006, Riga, Latvia

    V. G. Andrianov

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    B. B. Averkiev & M. Yu. Antipin

Authors
  1. A. B. Sheremetev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. G. Andrianov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Mantseva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. V. Shatunova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. S. Aleksandrova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. L. Yudin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. D. E. Dmitriev
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. B. B. Averkiev
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. M. Yu. Antipin
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sheremetev, A.B., Andrianov, V.G., Mantseva, E.V. et al. Synthesis of secondary and tertiary aminofurazans. Russian Chemical Bulletin 53, 596–614 (2004). https://doi.org/10.1023/B:RUCB.0000035644.16331.f0

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUCB.0000035644.16331.f0

Search

Navigation