Skip to main content
SpringerLink
Log in

Reactions of dimethyl 2-chloroethynylphosphonate with 1-substituted 5-oxo-1H-1,2,3,4-tetrazoles

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

Abstract

Addition of 1-substituted tetrazol-5-ones to dimethyl 2-chloroethynylphosphonate occurred regioselectively to form new geminally substituted bis(4-R-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethenylphosphonates with 65–92% yield.

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. Raboisson, P., Baurand, A., Cazenave, J.-P., Gachet, C., Schutz, D., Spiess, B., and Bourguigon, J.-J., J. Org. Chem., 2002, vol. 67, p. 8063. DOI: 10.1021/jo026268l.

    Article  CAS  Google Scholar 

  2. Holstein, S.A., Cermak, D.M., Wiemer, D.F., Lewis, K., and Hohl, R., J. Bioorg. Med. Chem., 1998, vol. 6, p. 687. DOI: 10.1016/S0968-0896(98)00034-0.

    Article  CAS  Google Scholar 

  3. Lazrek, H.B., Rochdi, A., Khaider, H., Barascut, J.L., Imbach, J.L., Balzarini, J., Witvrouw, M., Pannecouque, C., and De Clerq, E., Tetrahedron, 1998, vol. 54, p. 3807. DOI: 10.1016/S0040-4020(98)00107-0.

    Article  CAS  Google Scholar 

  4. Harnden, M.R., Parkin, A., Parratt, M.J., and Perkins, R.M., J. Med. Chem., 1993, vol. 36, p. 1343. DOI: 10.1021/jm00062a006.

    Article  CAS  Google Scholar 

  5. Welch, C.M., Gozalez, E.J., and Guthrie, J.D., J. Org. Chem., 1961, vol. 26, p. 3270. DOI: 10.1021/jo01067a057.

    Article  CAS  Google Scholar 

  6. Jin J.I., US Patent 74-496233, 1978; C. A., 1979, no. 90, 153010m.

  7. Cristau, H.-J., Pirat, J.-L., Drag, M., and Kafarski, P., Tetrahedron Lett., 2000, vol. 41, p. 9781. DOI: 10.1016/S0040-4039(00)01723-8.

    Article  CAS  Google Scholar 

  8. Inoue, H., Tsubouchi, H., Nagaoka, Y., and Tomioka, K., Tetrahedron, 2002, vol. 58, p. 83. DOI: 10.1016/S0040-4020(01)01089-4.

    Article  CAS  Google Scholar 

  9. Ranu, B.C., Guchhait, S.K., and Ghosh, K.J., Org. Chem., 1998, vol. 63, p. 5250. DOI: 10.1021/jo980128n.

    Article  CAS  Google Scholar 

  10. Petrov, A.A., Dogadina, A.V., Ionin, B.I., Garibina, V.A., and Leonov, A.A., Russ. Chem. Rev., 1983, vol. 52, no. 11, p. 1030.

    Article  Google Scholar 

  11. Garibina, V.A., Leonov, A.A., Dogadina, A.V., Ionin, B.I., and Petrov, A.A., Zh. Obsch. Khim., 1985, vol. 55, no. 9, p. 1994.

    CAS  Google Scholar 

  12. Garibina, V.A., Leonov, A.A., Dogadina, A.V., Ionin, B.I., and Petrov, A.A., Zh. Obsch. Khim., 1987, vol. 57, no. 7, p. 1481.

    CAS  Google Scholar 

  13. Erkhitueva, E.B., Dogadina, A.V., Khramchikhin, A.V., and Ionin, B.I., Tetrahedron Lett., 2013, vol. 54, no. 38, p. 5174. DOI: 10.1016/j.tetlet.2013.07.032.

    Article  CAS  Google Scholar 

  14. Han, S.Y., Lee, J.W., Kim, H.-J., Kim, Y.-J., Lee, S.W., and Gyoung, Y.S., Bull. Korean Chem. Soc., 2012, vol. 33, no. 1, p. 55.

    Article  CAS  Google Scholar 

  15. Lieber, E., and Ramachandran, J., Canad. J. Chem., 1959, vol. 37, p. 101.

    Article  CAS  Google Scholar 

  16. Koreneva, A.P. and Koldobskii, G.I., Zh. Org. Khim., 1999, vol. 35, no. 10, p. 1542.

    Google Scholar 

  17. Ostrovskii, V.A. and Koren, A.O., Heterocycles, 2000, vol. 53, p. 1421.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State University of Technology and Design, St. Petersburg, Russia

    Yu. V. Mel’nikova & L. V. Myznikov

  2. St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. V. Dogadina & N. I. Svintsitskaya

Authors
  1. Yu. V. Mel’nikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. V. Myznikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Dogadina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. I. Svintsitskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. I. Svintsitskaya.

Additional information

Original Russian Text © Yu.V. Mel’nikova, L.V. Myznikov, A.V. Dogadina, N.I. Svintsitskaya, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 11, pp. 1863–1869.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mel’nikova, Y.V., Myznikov, L.V., Dogadina, A.V. et al. Reactions of dimethyl 2-chloroethynylphosphonate with 1-substituted 5-oxo-1H-1,2,3,4-tetrazoles. Russ J Gen Chem 84, 2160–2166 (2014). https://doi.org/10.1134/S107036321411019X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107036321411019X

Keywords

Search

Navigation