Skip to main content
SpringerLink
Log in

Reactions of Activated Enynes with Diazomethane

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

Abstract

Electron-deficient conjugated enynes reacted with diazomethane under mild conditions at the C=C double bond to give the corresponding nitrogen-containing cycloadducts or cyclopropanes. The product structure depended on the number of electron-withdrawing groups at the double bond of the initial enyne. 1,5-Diarylpent-2-en-4-yn-1-ones were converted to 4,5-dihydro-1H-pyrazoles, propargylidenemalonic acid derivatives gave rise to 4,5-dihydro-3H-pyrazoles, and 5,7-dioxaspiro[2.5]octane-4,8-diones were formed from enyne derivatives of Meldrum’s acid. Noncatalytic methods were developed for the synthesis of spirocyclic cyclopropanes and ethynyl-substituted dihydropyrazoles in 75–90% yields.

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

Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Breugst, M., Huisgen, R., and Reissig, H.-U., Eur. J. Org. Chem., 2018, vol. 2018, p. 2477. https://doi.org/10.1002/ejoc.201800100

    Article  CAS  Google Scholar 

  2. Menchikov, L.G., Shulishov, E.V., and Tomilov, Yu.V., Russ. Chem. Rev., 2021, vol. 90, p. 199. https://doi.org/10.1070/RCR4982

    Article  CAS  Google Scholar 

  3. Latypova, D.R., Dokichev, V.A., and Zlotskii, S.S., Uspekhi khimii diazosoedinenii. Metody polucheniya, reaktsii, svoistva (Advances in the Chemistry of Diazo Compounds. Methods of Synthesis, Reactions, and Properties), Saarbryukken: Lambert Academic Publishing, 2012, p. 7.

  4. Yang, H., Martin, B., and Shenkel, B., Org. Process Res. Dev., 2018, vol. 22, p. 446. https://doi.org/10.1021/acs.oprd.7b00302

    Article  CAS  Google Scholar 

  5. Proctor, L.D. and Warr, A.J., Org. Process Res. Dev., 2002, vol. 6, p. 884. https://doi.org/10.1021/op020049k

    Article  CAS  Google Scholar 

  6. Bennani, F.E., Doudach, L., Cherrah, Y., Ramli, Y., Karrouchi, K., Ansar, M., and Faouzi, M.E.A., Bioorg. Chem., 2020, vol. 97, article ID 103470. https://doi.org/10.1016/j.bioorg.2019.103470

  7. Salaün, J., Small Ring Compounds in Organic Synthesis VI, de Meijere, A., Ed., 2000, p. 1. https://doi.org/10.1007/3-540-48255-5

  8. Korobitsyna, I.K., Bulusheva, V.V., and Rodina, L.L., Chem. Heterocycl. Compd., 1978, vol. 14, p. 471. https://doi.org/10.1007/BF00673325

    Article  Google Scholar 

  9. Bettinetti, G., Desimoni, G., and Grunanger, P., Gazz. Chem. Ital., 1964, vol. 94, p. 91.

    CAS  Google Scholar 

  10. Vo-Quang, L. and Vo-Quang, Y., Bull. Soc. Chim. Fr., 1974, p. 2575.

  11. Reimlinger, H. and Moussebois, C.H., Chem. Ber., 1965, vol. 98, p. 1805. https://doi.org/10.1002/cber.19650980619

    Article  CAS  Google Scholar 

  12. Yangirov, T.A., Cand. Sci. (Chem.) Dissertation, Ufa. 2013.

  13. Golovanov, A.A., Odin, I.S., and Zlotskii, S.S., Russ. Chem. Rev., 2019, vol. 88, p. 280. https://doi.org/10.1070/RCR4808

    Article  CAS  Google Scholar 

  14. Golovanov, A.A., Gusev, D.M., Odin, I.S., and Zlot­skii, S.S., Chem. Heterocycl. Compd., 2019, vol. 55, p. 333. https://doi.org/10.1007/s10593-019-02462-0

    Article  CAS  Google Scholar 

  15. Odin, I.S., Golovanov, A.A., Bekin, V.V., and Pisa­re­va, V.S., Chem. Heterocycl. Compd., 2014, vol. 49, p. 1687. https://doi.org/10.1007/s10593-014-1421-7

    Article  CAS  Google Scholar 

  16. Sokov, S.A., Odin, I.S., Gusev, D.M., Kunavin, Yu.A., Vologzhanina, A.V., Voronova, E.D., and Golova­nov, A.A., Russ. Chem. Bull., Int. Ed., 2020, vol. 69, p. 305. https://doi.org/10.1007/211172-020-2761-3

    Article  CAS  Google Scholar 

  17. Maurya, R.A., Kapure, J.S., Adiyala, P.R., Srikanth, P.S., Chandrasekhar, D., and Kamal, A., RSC Adv., 2013, vol. 3, p. 15600. https://doi.org/10.1039/C3RA42374C

    Article  CAS  Google Scholar 

  18. Klimova, V.A., Osnovnye mikrometody analiza organicheskikh soedinenii (Main Micro Methods for Analysis of Organic Compounds), Moscow: Khimiya, 1975, p. 51.

  19. Shulishov, E.V., Klimenko, I.P., and Tomilov, Yu.V., Sintezy organicheskikh soedinenii (Syntheses of Organic Compounds), Moscow: Maks Press, 2008, vol. 3.

  20. Golovanov, A.A., Latypova, D.R., Bekin, V.V., Pisa­reva, V.S., Vologzhanina, A.V., and Dokichev, V.A., Russ. J. Org. Chem., 2013, vol. 49, p. 1264. https://doi.org/10.1134/S1070428013090030

    Article  CAS  Google Scholar 

  21. Sokov, S.A., Odin, I.S., Zlotskii, S.S., and Golova­nov, A.A., Russ. J. Org. Chem., 2020, vol. 56, p. 1758. https://doi.org/10.1134/S1070428020100140

    Article  Google Scholar 

  22. Saulnier, S., Golovanov, A.A., Ivanov, A.Yu., Boyarskaya, I.A., and Vasilyev, A.V., J. Org. Chem., 2016, vol. 81, p. 1967. https://doi.org/10.1021/acs.joc.5b02785

    Article  CAS  PubMed  Google Scholar 

  23. Golovanov, A.A., Dan’kov, S.A., Sokov, S.A., Melni­kov, P.A., Ukolov, A.I., Voronova, E.D., Vologzha­nina, A.V., and Bunev, A.S., Chem. Heterocycl. Compd., 2019, vol. 55, p. 93. https://doi.org/10.1007/s10593-019-02424-6

    Article  CAS  Google Scholar 

  24. Belil, C., Pascual, J., and Serratosa, F., Tetrahedron, 1964, vol. 20, p. 2701. https://doi.org/10.1016/S0040-4020(01)90851-8

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors thank K.V. Gordon for performing elemental analyses.

Funding

This study was performed under financial support by the Leader Project Competition of the Ufa State Petroleum Technological University (nomination “Scientific Research Foundation”).

Author information

Authors and Affiliations

  1. Ufa State Petroleum Technological University, 450064, Ufa, Russia

    S. A. Sokov & S. S. Zlotski

  2. Togliatti State University, 445020, Togliatti, Russia

    S. A. Sokov, I. S. Odin, A. G. Denisova & A. A. Golovanov

Authors
  1. S. A. Sokov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. S. Odin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. S. Zlotski
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. G. Denisova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Golovanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. A. Golovanov.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1371–1381 https://doi.org/10.31857/S0514749221100025.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sokov, S.A., Odin, I.S., Zlotski, S.S. et al. Reactions of Activated Enynes with Diazomethane. Russ J Org Chem 57, 1575–1583 (2021). https://doi.org/10.1134/S107042802110002X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042802110002X

Keywords:

Search

Navigation