Skip to main content
SpringerLink
Log in

Unexpected direction in the cyclization of α,α'-diaminated cyclopentanone with malonic dialdehyde tetramethyl acetal

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

New compounds were unexpectedly discovered in a detailed study of the cyclization of α-aminated carbocyclic ketones with malonic dialdehyde tetramethyl acetal, in addition to the formation of the corresponding pyrazoles. In the case of cyclopentanone these new products are 6,7-dihydro-2H-cyclo-penta[c]pyridazine-4-carbaldehyde and 3-hydroxy-2,2-di(1H-pyrazol-1-yl)cyclopentanone. For cyclo-hexanone, the intermediate in the cyclization to a pyrazole, namely, the tert-butyl ester of 1-(2-oxo-cyclohexyl)-2-(3-oxoprop-1-en-1-yl)hydrazinecarboxylic acid, was isolated.

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

Similar content being viewed by others

References

  1. A. V. Kurkin, A. A. Utkina, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 127 (2008). [Chem. Heterocycl. Compd., 44, 106 (2008)].

    Google Scholar 

  2. B. List, J. Am. Chem. Soc., 124, 5656 (2002).

    Article  CAS  Google Scholar 

  3. A. A. Utkina, A. V. Kurkin, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 347 (2012). [Chem. Heterocycl. Compd., 48, 327 (2012)].

    Google Scholar 

  4. Y. Hayashi, S. Aratake, Y. Imai, K. Hibino, Q.-Y. Chen, Y. Yamaguchi, and T. Uchimaru, Chem.-Asian J., 3, 225 (2008).

    Article  CAS  Google Scholar 

  5. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

    Article  CAS  Google Scholar 

  6. V. B. Rybakov, A. A. Utkina, A. V. Kurkin, and M. A. Yurovskaya, Acta Crystallogr., Sect. E: Struct. Rep. Online, E68, o844 (2012).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 1 Build. 3 Leninskie Gory, Moscow, 119991, Russia

    A. A. Utkina, A. V. Kurkin & M. A. Yurovskaya

Authors
  1. A. A. Utkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Kurkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Yurovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. A. Utkina.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 960-964, June, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Utkina, A.A., Kurkin, A.V. & Yurovskaya, M.A. Unexpected direction in the cyclization of α,α'-diaminated cyclopentanone with malonic dialdehyde tetramethyl acetal. Chem Heterocycl Comp 48, 892–896 (2012). https://doi.org/10.1007/s10593-012-1072-5

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-1072-5

Keywords

Search

Navigation