Skip to main content
SpringerLink
Log in

Nucleophile-induced transformations of 1,2,4-triazines. 3. Anrorc constriction of the ring in the reaction of 6-aryl-3-dimethylamino-1,2,4-triazine 4-oxides with KCN

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Reaction of 6-aryl-3-dimethylamino-1,2,4-triazine 4-oxides with KCN results in constriction of the heterocycle and formation of 3-amino-5-aryl-4-nitrosopyrazoles. Several methods including labelled K13C15N are used to demonstrate that the reaction proceeds through the ANRORC mechanism.

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. O. N. Chupakhin, V. N. Kozhevnikov, D. N. Kozhevnikov, and V. L. Rusinov,Zh. Org. Khim.,34, 418 (1998).

    Google Scholar 

  2. O. N. Chupakhin, V. N. Charushin, and H. C. van der Plas,Nucleophilic Aromatic Substitution of Hydrogen, Academic Press, New York and San Diego (1994).

    Google Scholar 

  3. H. C. van der Plas,Acc. Chem. Res.,11, 462 (1978).

    Google Scholar 

  4. H. C. van der Plas,Ring Transformations of Heterocycles, Academic Press, New York (1973).

    Google Scholar 

  5. V. N. Kozhevnikov, D. N. Kozhevnikov, I. S. Kovalev, V. L. Rusinov, and O. N. Chupakhin, in: Abstracts of Papers of the International Scientific Conference “Organic Synthesis and Combinatorial Chemistry,” Zvenigorod, March 4–7, 1999, Moscow.

  6. D. N. Kozhevnikov, V. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin, E. O. Sidorov, and N. A. Klyuev,Zh. Org. Khim.,34, 423 (1998).

    Google Scholar 

  7. O. N. Chupakhin, V. L. Rusinov, E. N. Ulomsky, D. N. Kojevnikov, and H. Neunhoeffer,Mendeleev Commun., No. 2, 66 (1997).

    Google Scholar 

  8. A. Rykowski and E. Wolinska,Tetrahedron Lett.,37, 5795 (1996).

    Google Scholar 

Download references

Authors
  1. V. N. Kozhevnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. N. Kozhevnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. N. Chupakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Dedicated to Professor Henk van der Plas on his 70th birthday.

For No. 2, see [1].

Urals State Technical University, Ekaterinburg 620002, Russia; e-mail: mike@htf.ustu.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 532–535, April, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kozhevnikov, V.N., Kozhevnikov, D.N., Rusinov, V.L. et al. Nucleophile-induced transformations of 1,2,4-triazines. 3. Anrorc constriction of the ring in the reaction of 6-aryl-3-dimethylamino-1,2,4-triazine 4-oxides with KCN. Chem Heterocycl Compd 35, 470–473 (1999). https://doi.org/10.1007/BF02319336

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02319336

Keywords

Search

Navigation