Skip to main content
SpringerLink
Log in

Non-catalytic Addition of 1,2,4-Triazole to Nucleophilic and Electrophilic Alkenes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Non-catalytic addition of 1,2,4-triazole to vinyl ethers and esters occurs on heating (65-175°C, 4-20 h) to give Markovnikov adducts (yield 30-100%). Electron-deficient alkenes (acrylonitrile, acrylic acid, 4-phenyl-3-buten-2-one) react with 1,2,4-triazole (78-190°C, 4-20 h) to give anti-Markovnikov adducts in yields of 45-83%.

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. A. R. Katritzky, J. Heterocycl. Chem., 36, 1501 (1999).

    Google Scholar 

  2. H. Wamhoff, Comp. Heterocycl. Chem., 5, 4 (1984).

    Google Scholar 

  3. Y. Yang, L. Wenshuo, and S. Yannian, Chemistry (Huaxue Tongbao), No. 10, 6 (1966); Ref. Zh. Khim., 40397 (1998).

  4. K. Tomoyuki, I. Takashi, T. Akihiro, H. Hiroshi, M. Yoshihiro, H. Ryogo, O. Kenji, and I. Katsumi, Chem. Pharm. Bull., 48,12, 1935 (2000).

    Google Scholar 

  5. I. V. Mashevskaya, L. V. Aniskina, Yu. B. Vikharev, V. A. Safin, S. V. Kol'tsova, and A. N. Maslivets, Khim-farm. Zh., 35, No 1, 11 (2001).

    Google Scholar 

  6. M. Butters, J. Ebbs, S. Green, J. MacRae, M. Morland, C. Murtiashaw, and A. Pettman, Org. Process Res. Dev., 5, 28 (2001).

    Google Scholar 

  7. French Pat. 2802530 (1999); Ref. Zh. Khim., 1O133P (2002).

  8. German Pat. 19941650 (1999); Ref. Zh. Khim., 1H83P (2002).

  9. J. Stetter and F. Lied, Angew. Chem. Int. Ed., 39, 1725 (200).

    Google Scholar 

  10. A. M. Belousov, G. A. Gareev, L. P. Kirillova, and L. I. Vereshchagin, Zh. Org. Khim., 16, 2622 (1980).

    Google Scholar 

  11. R. H. Wiley, N. R. Smith, D. M. Johnson, and J. Moffatt, J. Am. Chem. Soc., 77, 19, 2572 (1955).

    Google Scholar 

  12. R. H. Wiley, N. R. Smith, D. M. Johnson, and J. Moffatt, J. Am. Chem. Soc., 76,19, 4933 (1954).

    Google Scholar 

  13. B. I. Mikhantyev, V. B. Mikhantyev, V. L. Lapenko, and V. K. Voinova, Some Vinyl Monomers [in Russian], Voronezh Univ. Press, Voronezh (1970), 197.

    Google Scholar 

  14. D. Barton and J. D. Ollis (editors), General Organic Chemistry [Russian translation], Khimiya, Moscow (1985), 8, 437.

    Google Scholar 

  15. M. F. Shostakovskii, Vinyl Ethers [in Russian], Publ. House of USSR Academy of Sciences, Moscow (1952).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Irkutsk State University, Irkutsk, 664000, Russia

    B.V. Timokhin, A. I. Golubin & V. A. Kron

  2. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    O. V. Vysotskaya, L. A. Oparina, N. K. Gusarova & B. A. Trofimov

Authors
  1. B.V. Timokhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. I. Golubin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Vysotskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. A. Kron
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. A. Oparina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. N. K. Gusarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. B. A. Trofimov
    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

Timokhin, B., Golubin, A.I., Vysotskaya, O.V. et al. Non-catalytic Addition of 1,2,4-Triazole to Nucleophilic and Electrophilic Alkenes. Chemistry of Heterocyclic Compounds 38, 981–985 (2002). https://doi.org/10.1023/A:1020981816097

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1020981816097

Search

Navigation