Skip to main content
SpringerLink
Log in

Epichlorohydrin as a Precursor of Functionally Substituted 1,2,3-Triazoles and Tetrazoles

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

Abstract

Different procedures for azidation of epichlorohydrin and 2-(oxiran-2-ylmethyl)-5-phenyltetrazole in aqueous medium are considered. The synthetic potential of 1-azido-3-chloropropan-2-ol is demonstrated by its reactions with NH-unsubstituted azoles and 1.3-dipolar cycloaddition to ethynyl dipolarophiles.

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. Fringuelli, F., Piermatti, O., Pizzo, F., and Vaccaro, L., J. Org. Chem., 1999, vol.64, p.6094. doi https://doi.org/10.1021/jo990368i

    Article  CAS  Google Scholar 

  2. Vyvyan, J.R., Meyer, J.A., and Meyer, K.D., J. Org. Chem., 2003, vol.68, p.9144. doi https://doi.org/10.1021/jo035112y

    Article  CAS  PubMed  Google Scholar 

  3. Wang, Zh., Cui, Y-T., Xu, Zh-B., and Qu, J., J. Org. Chem., 2008, vol.73, p.2270. doi https://doi.org/10.1021/jo702401t

    Article  CAS  PubMed  Google Scholar 

  4. Fringuelli, F., Pizzo, F., Tortoioli, S., and Vaccaro, L., J. Org. Chem., 2003, vol.68, p.8248. doi https://doi.org/10.1021/jo0348266

    Article  CAS  PubMed  Google Scholar 

  5. Golobokova, T.V., Projdakova, A.G., Vereshchagin, L.I., and Kizhnyaev, V.N., Russ. J. Org. Chem., 2015, vol.51, p.1308. doi https://doi.org/10.1134/S1070428015090171

    Article  CAS  Google Scholar 

  6. Alonso, G., Garcia-Lopez, M.T., Garcia-Munoz, G., Madronero, R., and Rico, M., J. Heterocycl. Chem., 1970, vol.7, p.1269. doi https://doi.org/10.1002/jhet.5570070606

    Article  CAS  Google Scholar 

  7. Verhozina, O.N., Kizhnyaev, V.N., Vereshchagin, L.I., Rohin, A.V., and Smirnov, A.I., Russ. J. Org. Chem., 2003, vol.39, p.1792. doi https://doi.org/10.1023/B:RUJO.0000019746.10504.f3

    Article  Google Scholar 

  8. Koldobskii, G.I., Ostrovskii, V.A., and Poplavskii, V.S., Chem. Heterocycl. Comp., 1981, vol.17, p.965. doi https://doi.org/10.1007/BF00503523

    Article  Google Scholar 

  9. Kitaeva, V.G., Beresnev, D.G., Ishmetova, R.I., and Rusinov, G.L., Zh. Org. Khim., 1995, vol.31, p.620.

    CAS  Google Scholar 

  10. Golobokova, T.V., Vereshchagin, L.I., Ratovskii, G.V., Projdakov, A.G., and Kizhnyaev, V.N., Russ. J. Org. Chem., 2016, vol.52, p.1039. doi https://doi.org/10.1134/S107042801607021

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Irkutsk State University, ul. K. Marksa 1, Irkutsk, 664003, Russia

    T. V. Golobokova, A. G. Proidakov, L. I. Vereshchagin & V. N. Kizhnyaev

Authors
  1. T. V. Golobokova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. G. Proidakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. I. Vereshchagin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. N. Kizhnyaev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. V. Golobokova.

Additional information

Russian Text © T.V. Golobokova, A.G. Proidakov, L.I. Vereshchagin, V.N. Kizhnyaev, 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 2, pp. 234–241.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Golobokova, T.V., Proidakov, A.G., Vereshchagin, L.I. et al. Epichlorohydrin as a Precursor of Functionally Substituted 1,2,3-Triazoles and Tetrazoles. Russ J Org Chem 55, 186–192 (2019). https://doi.org/10.1134/S1070428019020106

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019020106

Keywords

Search

Navigation