Skip to main content
SpringerLink
Log in

Synthesis of New 5-Mercapto-1,3-oxazole Derivatives on the Basis of 2-Acylamino-3,3-dichloroacrylonitriles and Their Analogs

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Enamides of the general formula Cl2CÍC(X)NHCOR1, where X = CN, COOAlk, CONH2, P(O)(OEt)2, P(O)Ph2, +PPh3 Cl-, were treated in succession with alkane- or arenethiols and silver carbonate to obtain 5-alkyl(aryl)thio-2-R1-4-X-1,3-oxazoles with high selectivity. The latter were converted into the corresponding sulfonyl derivatives. Unlike 2-acylamino-3,3-dichloroacrylonitriles which react with sodium hydrogen sulfide in a nonselective fashion, reactions of derivatives like Cl(ArS)CÍC(CN)NHCOR1 with NaHS lead to hitherto unknown 5-arylthio-4-thiocarbamoyl-2-R1-1,3-oxazoles whose structure was confirmed both by spectral methods and by cyclocondensation with bromoacetophenone according to Hantzsch. Heating of some 2-aryl-5-mercapto-4-X-1,3-oxazoles with benzenethiols results in recyclization into the corresponding 2,4-disubstituted 5-arylthio-1,3-thiazoles, presumably due to prototropic tautomerism in the 5-mercaptooxazole fragment.

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

REFERENCES

  1. Drach, B.S., Brovarets, V.S., and Smolii, O.B., Sintezy azotsoderzhashchikh soedinenii na osnove amidoalkiliruyushchikh agentov (Syntheses of Nitrogen-Containing Compounds on the Basis of Amidoalkylating Agents), Kiev: Naukova Dumka, 1992, pp. 81-91.

    Google Scholar 

  2. Matsumura, K., Miyashita, O., Shimadzu, H., and Hashimoto, N., Chem. Pharm. Bull., 1976, vol. 24, no. 5, p. 948.

    Google Scholar 

  3. Drach, B.S. and Mis'kevich, G.N., Zh. Org. Khim., 1977, vol. 13, no. 7, p. 1398.

    Google Scholar 

  4. Lobanov, O.P., Martynyuk, A.P., and Drach, B.S., Zh. Obshch. Khim., 1980, vol. 50, no. 10, p. 2248.

    Google Scholar 

  5. Vinogradova, T.K., Kisilenko, A.A., and Drach, B.S., Zh. Org. Khim., 1982, vol. 18, no. 9, p. 1864.

    Google Scholar 

  6. Brovarets, V.S., Vydzhak, R.N., and Drach, B.S., Zh. Obshch. Khim., 1993, vol. 63, no. 5, p. 1053.

    Google Scholar 

  7. Kurg, V.V., Brovarets, V.S., and Drach, B.S., Zh. Obshch. Khim., 1991, vol. 61, no. 4, p. 874.

    Google Scholar 

  8. Matsumura, K., Saraie, T., and Hashimoto, N., Chem. Pharm. Bull., 1976, vol. 24, no. 5, p. 912.

    Google Scholar 

  9. Drach, B.S., Sviridov, E.P., Kisilenko, A.A., and Kirsanov, A.V., Zh. Org. Khim., 1973, vol. 9, no. 9, p. 1818.

    Google Scholar 

  10. Drach, B.S., Sviridov, E.P., and Lavrenyuk, T.Ya., Zh. Org. Khim., 1974, vol. 10, no. 6, p. 1271.

    Google Scholar 

  11. Drach, B.S. and Mis'kevich, G.N., Zh. Org. Khim.,1978, vol. 14, no. 3, p. 501.

    Google Scholar 

  12. Drach, B.S. and Mis'kevich, G.N., Zh. Org. Khim., 1974, vol. 10, no. 11, p. 2315.

    Google Scholar 

  13. Drach, B.S., Sviridov, E.P., and Shaturskii, Ya.P., Zh. Obshch. Khim., 1974, vol. 44, no. 8, p. 1712.

    Google Scholar 

  14. Drach, B.S., Sviridov, E.P., and Kirsanov, A.V., Zh. Obshch. Khim., 1975, vol. 45, no. 1, p. 12.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Bioorganic and Petroleum Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine

    S. G. Pil'o, V. S. Brovarets, T. K. Vinogradova, A. V. Golovchenko & B. S. Drach

Authors
  1. S. G. Pil'o
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. S. Brovarets
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. K. Vinogradova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Golovchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. B. S. Drach
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pil'o, S.G., Brovarets, V.S., Vinogradova, T.K. et al. Synthesis of New 5-Mercapto-1,3-oxazole Derivatives on the Basis of 2-Acylamino-3,3-dichloroacrylonitriles and Their Analogs. Russian Journal of General Chemistry 72, 1714–1723 (2002). https://doi.org/10.1023/A:1023333011230

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1023333011230

Keywords

Search

Navigation