Skip to main content
SpringerLink
Log in

Synthesis and reactions of β-lactones

XV. Reaction of β-trichloromethyl-β-propiolactone with α-amino heterocyclic nitrogen compounds

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In contrast to β-propiolactone and diketene, β-trichloromethyl-β-propiolactone generally reacts with α-amino heterocyclic nitrogen compounds to give amides of 3-hydroxy-4,4,4-trichlorobutyric acid (with the participation of the exocyclic and endocyclic nitrogen atoms of the reagents) rather than condensed heterocycles (pyrimidine derivatives). The reasons for the difference in the reactivities of the indicated β-lactones are discussed.

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

Literature cited

  1. F. I. Luknitskii, D. O. Taube, and B. A. Vovsi, Zh. Organ. Khim., 5, 1851 (1969).

    Google Scholar 

  2. F. I. Luknitskii, D. O. Taube, and B. A. Vovsi, Zh. Organ. Khim., 5, 1844 (1969).

    Google Scholar 

  3. F. I. Luknitskii and B. A. Vovsi, Zh. Organ. Khim., 3, 794 (1967).

    Google Scholar 

  4. F. I. Luknitskii and B. A. Vovsi, Zh. Organ. Khim., 3, 2142 (1967).

    Google Scholar 

  5. C. Hurd and S. Hayao, J. Am. Chem. Soc., 77, 117 (1955).

    Google Scholar 

  6. T. Kato, H. Yamanaka, and H. Moriya, Yakugaku Zasshi, 34, 1201 (1964); Chem. Abstr., 62, 7750 (1965).

    Google Scholar 

  7. G. Stöckelmann, H. Specker, and W. Riepe, Ber., 102, 455 (1969).

    Google Scholar 

  8. A. R. Katritzky (editor), Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Khimiya (1966), p. 617.

  9. A. R. Katritzky (editor), Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Khimiya (1966), p. 361.

  10. R. Adams and I Pachter, J. Am. Chem. Soc., 74, 9406 (1952).

    Google Scholar 

  11. M. Selim, O. Tetu, M. Selim, G. Martin, and P. Rumpf, Bull. Soc. Chim. France, 2117 (1968).

  12. K. Potts, Chem. Rev., 61, 87 (1961).

    Google Scholar 

  13. US Patent No. 2,403,329 (1949); Chem. Abstr., 44, 7174 (1950).

  14. D. Hoy and E. Poziomek, J. Org. Chem., 33, 4050 (1968).

    Google Scholar 

  15. L. Bellamy, Infra-Red Spectra of Complex Molecules, Methuen (1958).

  16. H. Staab and G. Seel, Ber., 92, 1302 (1959).

    Google Scholar 

  17. L. Birkofer, Ber., 76, 769 (1943).

    Google Scholar 

  18. K. Potts and T. Crawford, J. Org. Chem., 27, 2631 (1962).

    Google Scholar 

  19. E. Smolin and L. Rappoport, s-Triazines and Derivatives, New York (1959), p. 333.

Download references

Author information

Authors and Affiliations

  1. Leningrad Vitamin Combine, USSR

    F. I. Luknitskii & F. P. Shvartsman

Authors
  1. F. I. Luknitskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. F. P. Shvartsman
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for communication XIV.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 260–265, February, 1972.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Luknitskii, F.I., Shvartsman, F.P. Synthesis and reactions of β-lactones. Chem Heterocycl Compd 8, 235–239 (1972). https://doi.org/10.1007/BF00472367

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00472367

Keywords

Search

Navigation