Skip to main content
Log in

Synthesis of N-Substituted Thiazacycloalkanes by Cyclothiomethylation of Primary Aliphatic Amines and Amino Derivatives of Maleopimaric Acid

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

Abstract

Three-component cyclocondensation of primary aliphatic amines and amino derivatives of maleopimaric acid methyl ester with formaldehyde and carbochain (1,2-ethane-, 1,3-propane-, 1,4-butane-, 1,5-pentane-, 1,6-hexanedithiols) α,ω-dithiols or 3,6-dioxa-1,8-octanedithiol produced N-substituted thiazacycloalkanes.

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.

Similar content being viewed by others

References

  1. Khabibullina, G.R., Fedotova, E.S., Meshcheryakova, E.S., Buslaeva, T.M., Akhmetova, V.R., and Ibragimov, A.G., Chem. Heterocycl. Сompd., 2016, vol. 52, no. 10, p. 840. doi 1007/s10593-016-1975-7

    Article  CAS  Google Scholar 

  2. Khabibullina, G.R., Fedotova, E.S., Akhmetova, V.R., Mesheryakova, E.S., Khalilov, L.M., and Ibragimov, A.G., Mol. Divers., 2016, vol. 20, p. 557. doi https://doi.org/10.1007/s11030-016-9656-0

    Article  CAS  PubMed  Google Scholar 

  3. Khabibullina, G.R., Fedotova, Е.S., Abdullin, М.F., Tyumkina, Т.V., Akhmetova, V.R., and Ibragimov, A.G., Russ. J. Org. Chem., 2017, vol. 53, no. 2, p. 277. doi https://doi.org/10.1134/S1070428017020233

    Article  CAS  Google Scholar 

  4. Khabibullina, G.R., Akhmetova, V.R., Abdullin, M.F., Tyumkina, T.V., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron, 2014, vol. 70, p. 3502. doi https://doi.org/10.1016/j.tet.2014.03.053

    Article  CAS  Google Scholar 

  5. Khabibullina, G.R., Akhmetova, V.R., Fedotova, E.S., Nigmatullin, V.R., Nigmatullin, R.G., and Ibragimov, A.G., Petroleum Chem., 2016, vol. 56, no. 9, p. 879. doi https://doi.org/10.1134/S0965544116090085

    Article  CAS  Google Scholar 

  6. El-Sherief, H.A., Hozein, Z.A., El-Mahdy, F.M., and Sarhan, A.A., J. Heterocycl. Chem., 2010, vol. 47, p. 1294. doi https://doi.org/10.1002/jhet.471

    Article  CAS  Google Scholar 

  7. El Bialy, S.A.A., Abdelal, A.M., El-Shorbagi, A.-N., and Kheira, S.M.M., Arch. Pharm. Chem. Life Sci., 2005, vol. 338, p. 38. doi https://doi.org/10.1002/ardp.200400906

    Article  CAS  Google Scholar 

  8. Akhmetova, V.R., Anpilogova, G.R., Khabibullina, G.R., Akhmadiev, N.S., and Ibragimov, A.G., Russ. J. Appl. Chem., 2014, vol. 87, p. 585. doi https://doi.org/10.1134/S1070427214050085

    Article  CAS  Google Scholar 

  9. Tretyakova, E.V., Smirnova, I.E., Salimova, E.V., and Odinokov, V.N., Bioorg. Med. Chem., 2015, vol. 23, p. 6543. doi https://doi.org/10.1016/j.bmc.2015.09.006

    Article  CAS  PubMed  Google Scholar 

  10. Delevallee, F., Deraedt, R., and Benzoni, J., FR Patent 2586349A1, 1987.

    Google Scholar 

  11. Taylor, J.B., Ramm, P.J., and Fried, F., US Patent 3998823А, 1976.

    Google Scholar 

  12. Swikle, D.Ya., Kalninsh, A.Ya., Karklin’, R.Ya., Pruse, B.A., Prikule, A.Ya., Rumba, A.A., Rasinya, R.A., Shvinska, D.F., Baumane, G.K., and Kul’kevits, A.Ya., SU Patent 584722A1, 1994.

    Google Scholar 

  13. Kazakova, O.B., Tret’yakova, E.V., Kukovinets, O.S., Tolstikov, G.A., Nazyrov, T.I., Chudov, I.V., and Ismagilova, A.F., Russ. J. Bioorg. Chem., 2010, vol. 36, p. 762. doi https://doi.org/10.1134/S1068162010060130

    Article  CAS  Google Scholar 

  14. Tretyakova, E.V., Smirnova, I.E., Kazakova, O.B., Tolstikov, G.A., Yavorskaya, N.P., Golubeva, I.S., Pugacheva, R.B., Apryshko, G.N., and Poroikov, V.V., Bioorg. Med. Chem., 2014, vol. 22, p. 6481. doi https://doi.org/10.1016/j.bmc.2014.09.030

    Article  CAS  PubMed  Google Scholar 

  15. Wang, J., Chen, Y.P., Yao, K., Wilbon, P.A., Zhang, W., Ren, L., Zhou, J., Nagarkatti, M., Wang, Ch., Chu, F., He, X., Decho, A. W., and Tang, Ch., Chem. Commun., 2012, vol. 48, p. 916. doi https://doi.org/10.1039/C1CC16432E

    CAS  Google Scholar 

  16. Schuller, W.H., Minor, J.C., Block, S.S., and Lawrence, R.V., US Patent 3636215А, 1969.

    Google Scholar 

  17. Tret’yakova, E.V., Salimova, E.V., and Parfenova, L.V., Russ. J. Bioorg. Chem., 2018, vol. 44, no. 5, p. 547. doi https://doi.org/10.1134/S1068162018050175

    Article  Google Scholar 

  18. Wang, H., Wang, H., and Zhou, G., Polym Int., 2011, vol. 60, p. 557. doi https://doi.org/10.1002/pi.2978

    Article  CAS  Google Scholar 

  19. Rakhimova, E.B., Efremova, E.A., Bushmarinov, I.S., Goloveshkin, A.S., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron Lett., 2012, vol. 53, p. 4225. doi https://doi.org/10.1016/j.tetlet.2012.05.161

    Article  CAS  Google Scholar 

  20. Rakhimova, E.B., Ismagilov, R.A., Khalilov, L.M., Zainullin, R.A., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2015, vol. 51, p. 951. doi https://doi.org/10.1134/S1070428015070118

    Article  CAS  Google Scholar 

  21. Zalkow, L.H., Ford, R.A., and Kutney, J.P., J. Org. Chem., 1962, vol. 27, p. 3535. doi https://doi.org/10.1021/jo01057a031

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. R. Khabibullina.

Additional information

Russian Text © G.R. Khabibullina, E.S. Fedotova, E.V. Tretyakova, T.V. Tyumkina, L.V. Parfenova, A.G. Ibragimov, 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 1, pp. 31–38.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khabibullina, G.R., Fedotova, E.S., Tretyakova, E.V. et al. Synthesis of N-Substituted Thiazacycloalkanes by Cyclothiomethylation of Primary Aliphatic Amines and Amino Derivatives of Maleopimaric Acid. Russ J Gen Chem 89, 25–31 (2019). https://doi.org/10.1134/S1070363219010055

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219010055

Keywords

Navigation