Skip to main content
SpringerLink
Log in

Benzazolin-2-thiones in the michael reaction. 2. Reaction of benzothiazolin- and benzoxazolin-2-thiones with acrylonitrile, acrylamide, and methyl acrylate in the presence of basic catalysts

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Depending on the structure of the reagents and the kind of basic catalyst, the addition of benzazolin-2-thiones to an activated double bond takes place at either nitrogen or sulfur. Acrylonitrile, regardless of the catalyst, reacts at the nitrogen atom. In the presence of sodiummethylate, addition to acrylamide takes place only, and to methyl acrylate predominantly at nitrogen. In the presence of triethylamine, a mixture of compounds with a high content of S-derivatives forms.

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. K. V. Anan'eva and N. K. Rozhkova, Khim. Geterotsikl. Soedin., No. 4, 554 (1986).

    Google Scholar 

  2. A. F. Halasa and G. Smith, J. Org. Chem., 36, 636 (1971).

    Google Scholar 

  3. W. J. Humphlett, J. Heterocycl. Chem., 5, 387 (1968).

    Google Scholar 

  4. G. Sumrell, G. E. Ham, and E. D. Harnbaker, J. Am. Chem. Soc., 80, 2509 (1958).

    Google Scholar 

  5. V. Kalcheva and D. Dimov, Annual of Sofia University, 1969–1970, Vol. 64 (1972), p. 33.

    Google Scholar 

  6. B. Harman, US Patent 2,413,917; Chem. Abstr., 41, 2446 (1947).

    Google Scholar 

  7. C. D. Hurd and L. J. Gershbein, J. Amer. Chem. Soc., 69, 28 (1947).

    Google Scholar 

  8. G. Miyajima, K. Takahashi, and K. Nishimoto, Org. Magn. Reson., 6, 413 (1974).

    Google Scholar 

  9. J. J. Amico, J. Amer. Chem. Soc., 79, 5270 (1957).

    Google Scholar 

  10. N. A. Aliev, R. Aflyatunova, and K. Giyasov, In: Fungicides [in Russian], Fan, Tashkent (1980), p. 53.

    Google Scholar 

  11. K. V. Anan'eva and N. K. Rozhkova, All-Union Institute of Scientific and Technical Information, Academy of Sciences of the USSR, deposited paper No. 239-71; Ref. Zh. Khim., 9Zh99 (1972).

Download references

Author information

Authors and Affiliations

  1. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent

    K. V. Anan'eva & N. K. Rozhkova

Authors
  1. K. V. Anan'eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. K. Rozhkova
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For 1, see [1].

Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 688–690, May,

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 688–690, May,

Rights and permissions

Reprints and permissions

About this article

Cite this article

Anan'eva, K.V., Rozhkova, N.K. Benzazolin-2-thiones in the michael reaction. 2. Reaction of benzothiazolin- and benzoxazolin-2-thiones with acrylonitrile, acrylamide, and methyl acrylate in the presence of basic catalysts. Chem Heterocycl Compd 22, 564–567 (1986). https://doi.org/10.1007/BF00519541

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00519541

Keywords

Search

Navigation