Skip to main content
SpringerLink
Log in

Cyclization reactions of nitrils. 29. Regioselective synthesis of 6-aryl-3-cyano-2(1H)-pyridinethiones and the corresponding selenones and their characteristics

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The condensation of cyanothio- and cyanoselenoacetamide with 3-aryl-3-oxo-1-piperidino-1-propene or sodium 3-aryl-3-oxo-1-propen-1-olate takes place regioselectively with the formation of the 6-aryl-3-cyano-2(1H)-pyridinethiones or the corresponding selenones. Thieno[2,3-b]pyridines, thiazolo[3,2-a]pyridinium salts, and other annellated heterocycles were obtained from the 6-aryl-3-cyano-2(1H)-pyridinethiones.

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. Yu. A. Sharanin and G. V. Klokol, Zh. Org. Khim., 1986, in press.

  2. V. P. Litvinov, Yu. A. Sharanin, L. A. Rodinovskaya, A. M. Shestopalov, V. Yu. Mortikov, and V. K. Promonenkov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2760 (1984).

    Google Scholar 

  3. Yu. A. Sharanin, A. M. Shestopalov, V. K. Promonenkov, and L. A. Rodinovskaya, Zh. Org. Khim., 20, 2432 (1984).

    Google Scholar 

  4. Yu. A. Sharanin, A. M. Shestopalov, L. A. Rodinovskaya, V. K. Promonenkov, and V. P. Litvinov, Zh. Org. Khim., 20, 2442 (1984).

    Google Scholar 

  5. L. A. Rodinovskaya, Yu, A. Sharanin, V. P. Litvinov, V. K. Promonenkov, B. M. Zolotarev, and V. Yu. Mortikov, Zh. Org. Khim., 21, 2439 (1985).

    Google Scholar 

  6. V. P. Litvinov, Yu. A. Sharanin, V. K. Promonenkov, L. A. Rodinovskaya, A. M. Shestopalov, and V. Yu. Mortikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1869 (1984).

    Google Scholar 

  7. Yu. A. Sharanin, A. M. Shestopalov, V. K. Promonenkov, and L. A. Rodinovskaya, Zh. Org. Khim., 20, 1539 (1984).

    Google Scholar 

  8. H. Günther, NMR Spectroscopy. An Introduction, Wiley, New York (1980).

    Google Scholar 

  9. V. K. Promonenkov, A. M. Shestopalov, Yu. A. Sharanin, V. P. Litvinov, L. A. Rodinovskaya, B. M. Zolotarev, V. D. Sokovykh, B. V. Rozynov, and Ya. Ya. Krymskii, Zh. Org. Khim., 21, 1963 (1985).

    Google Scholar 

  10. D. Barton and W. D. Ollis (eds.), Comprehensive Organic Chemistry, Vol. 8, Pergamon Press Elmsford, N.Y. (1985).

    Google Scholar 

  11. V. P. Litvinov, V. K. Promonenkov, Yu. A. Sharanin, A. M. Shestopalov, L. A. Rodinovskaya, V. Yu. Mortikov, and V. S. Bogdanov, Izv. Akad. Nauk SSSR. Ser. Khim., No. 9, 2101 (1985).

    Google Scholar 

  12. B. Blank, N. W. Di Tullio, J. A. Krog, and J. H. Saunders, J. Med. Chem., 21, 489 (1978).

    Google Scholar 

  13. F. S. Babichev (ed.), Intramolecular Interaction of Nitrile and CH, OH, and SH Groups [in Russian], Naukova Dumka, Kiev (1985), p. 200.

    Google Scholar 

  14. V. I. Staninets and E. A. Shilov, Usp. Khim., 40, 491 (1971).

    Google Scholar 

  15. Yu. I. Gevaza and V. I. Staninets, Khim. Geterotsikl. Soedin., No. 4, 435 (1985).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. T. G. Shevchenko Voroshilovgrad State Pedagogical Institute, USSR

    L. A. Rodinovskaya, Yu. A. Sharanin, A. M. Shestopalov & V. P. Litvinov

Authors
  1. L. A. Rodinovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. A. Sharanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. M. Shestopalov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. P. Litvinov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication 28, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 805–812, June, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rodinovskaya, L.A., Sharanin, Y.A., Shestopalov, A.M. et al. Cyclization reactions of nitrils. 29. Regioselective synthesis of 6-aryl-3-cyano-2(1H)-pyridinethiones and the corresponding selenones and their characteristics. Chem Heterocycl Compd 24, 658–665 (1988). https://doi.org/10.1007/BF00475603

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00475603

Keywords

Search

Navigation