Skip to main content
Log in

Reactions of 1,5-diketones. 42. Synthesis of heterocycles by the reaction of 4,4-dimethyl-1-phenyl-1-(2′-oxocycloalkyl)-3-pentanones with nitrogen-containing nucleophiles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 1,5-diketones containing a pivaloyl fragment with several nitrogen-containing nucleophiles was studied. Derivatives of 2-tert-butyl-1,4-dihydropyridine were obtained and the direction of heterocyclization upon the reaction of these diketones with primary amines containing an additional nucleophilic site was elucidated. The facile free-radical cleavage of the angular tert-butyl group was demonstrated.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. M. N. Tilichenko and N. N. Minaeva, Zh. Org. Khim.,19, 2516 (1983).

    Google Scholar 

  2. V. A. Kaminskii, I. V. Stepanchenko, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 9, 1251 (1979).

    Google Scholar 

  3. L. M. Eremeeva, T. V. Moskovkina, Yu. V. Vasilenko, A. N. Saverchenko, V. A. Kaminskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 2, 240 (1979).

    Google Scholar 

  4. V. A. Kaminskii, T. V. Zabolotnova, T. V. Novikova, and M. N. Tilichenko, Zh. Org. Khim.,17, 670 (1981).

    Google Scholar 

  5. G. Ferard, R. Ropert, M. Keravec, and P. F. Casals, Compt. Rend., C,279, 957 (1974).

    Google Scholar 

  6. H. S. Broadbent, W. S. Burnham, R. M. Sheeley, and R. K. Olsen, J. Heterocycl. Chem.,13, 337 (1976).

    Google Scholar 

  7. R. C. Elderfield and R. L. McClanahan, J. Am. Chem. Soc.,82, 1982 (1960).

    Google Scholar 

  8. K. J. Morgan, J. Chem. Soc., 2343 (1961).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Communication 41, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1664–1668, December, 1983.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kaminskii, V.A., Zabolotnova, T.V., Novikova, T.V. et al. Reactions of 1,5-diketones. 42. Synthesis of heterocycles by the reaction of 4,4-dimethyl-1-phenyl-1-(2′-oxocycloalkyl)-3-pentanones with nitrogen-containing nucleophiles. Chem Heterocycl Compd 19, 1316–1319 (1983). https://doi.org/10.1007/BF00842840

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00842840

Keywords

Navigation