Skip to main content
Log in

Reaction of (Z,E)-2-(Alkylsulfanyl)alk-2-en-4-ynals with N,N- and N,O-Binucleophiles

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

Abstract

The condensation of 2-alkylsulfanyl-substituted 2-en-4-ynals with N,N- and N,O-binucleophiles gives the corresponding 1,3-perhydrodiazines, 1,3-imidazolidines, and 1,3-oxazolidines with the original combination of substituents.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme
Scheme
Scheme

REFERENCES

  1. 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 

  2. 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 

  3. Igushkina, A.V., Golovanov, A.A., Boyarskaya, I.A., Kolesnikov, I.E., and Vasilyev, A.V., Molecules, 2020, vol. 25, p. 5920. https://doi.org/10.3390/molecules25245920

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Shechter, H. and Hoffman, R.V., J. Am. Chem. Soc., 1978, vol. 100, p. 7934. https://doi.org/10.1021/ja00493a024

    Article  Google Scholar 

  5. Shechter, H. J. Am. Chem. Soc. 1978, vol. 100, p. 7927. https://doi.org/10.1021/ja00493a023

  6. Shechter, H. and Hoffman, R.V., J. Org. Chem., 1974, vol. 39, p. 2939. https://doi.org/10.1021/jo00933a031

    Article  Google Scholar 

  7. Shechter, H. and Hoffman, R.V., J. Am. Chem. Soc., 1971, vol. 93, p. 5940. https://doi.org/10.1021/ja00751a082

    Article  Google Scholar 

  8. Bonrath, W., Buser, D., Pauling, H., and Thum, A., Molecules, 2002, vol. 7, p. 341. https://doi.org/10.3390/70300341

    Article  PubMed Central  Google Scholar 

  9. Li, Y., Sun, J., Zheng, G., Fu, Y., Wang, L., and Zhang, Q., Org. Lett., 2018, vol. 20, p. 5597. https://doi.org/10.1021/acs.orglett.8b02272

    Article  CAS  PubMed  Google Scholar 

  10. Fedoseeva, V.G., Verochkina, E.A., Larina, L.I., Kondrashov, E.V., Rozentsveig, I.B., and Vchislo, N.V., Mendeleev Commun., 2021, vol. 31, p. 856. https://doi.org/10.1016/j.mencom.2021.11.029

    Article  CAS  Google Scholar 

  11. Vchislo, N.V., Fedoseeva, V.G., Verochkina, E.A., and Larina, L.I., Polycycl. Arom. Compd., 2022, vol. 42, p. 7407. https://doi.org/10.1080/10406638.2021.2002375

    Article  CAS  Google Scholar 

  12. Keiko, N.A., Funtikova, E.A., Vchislo, N.V., Larina, N.V., and Frolov, Yu.L., Russ. J. Org. Chem., 2011, vol. 47, p. 1832. https://doi.org/10.1134/S1070428011120098

    Article  CAS  Google Scholar 

  13. Papernaya, L.K., Shatrova, A.A., Albanov, A.I., and Levkovskaya, G.G., Russ. J. Org. Chem., 2018, vol. 54, p. 734. https://doi.org/10.1134/S107042801805010X

    Article  CAS  Google Scholar 

  14. Man’kova, P.A., Reznikov, A.N., Shiryaev, V.A., Baimuratov, M.R., Rybakov, V.B., and Klimochkin, Yu.N., Russ. J. Org. Chem., 2021, vol. 57, p. 226. https://doi.org/10.1134/S1070428021020135

    Article  Google Scholar 

  15. Husain, A., Ahmad, A., Khan, S.A., Asif, M., Bhutani, R., and Al-Abbasi, F.A., Saudi Pharm. J., 2016, vol. 24, p. 104. https://doi.org/10.1016/j.jsps.2015.02.008

    Article  PubMed  Google Scholar 

Download references

ACKNOWLEDGMENTS

The work was performed using the equipment of the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences. The study was financially supported by the Russian Foundation for Basic Research (project no. 20-33-90022).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. V. Vchislo.

Ethics declarations

The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 2, pp. 271–276 https://doi.org/10.31857/S0514749223020155.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fedoseeva, V.G., Verochkina, E.A., Larina, L.I. et al. Reaction of (Z,E)-2-(Alkylsulfanyl)alk-2-en-4-ynals with N,N- and N,O-Binucleophiles. Russ J Org Chem 59, 332–336 (2023). https://doi.org/10.1134/S1070428023020161

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428023020161

Keywords:

Navigation