Skip to main content
SpringerLink
Log in

Synthesis of Macroheterocycles by Reaction of N,N′-(1,4-Phenylene)bis[N′-(4,4-diethoxybutyl)urea] with Resorcinol and Its Derivatives

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

Abstract

An efficient procedure has been developed for the synthesis of macroheterocycles by acid-catalyzed reaction of N,N′-(1,4-phenylene)bis[N′-(4,4-diethoxybutyl)urea] with resorcinol, 2-methylresorcinol, and pyrogallol. The structure of the isolated compounds was proved by spectral methods.

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

References

  1. Rajakumar, P. and Dhanasekaran, M., Tetrahedron, 2002, vol. 58, p. 1355.

    Article  CAS  Google Scholar 

  2. Stetson, C.M., Nishikawa, S., Purkiss, D.W., Dalley, N.K., and Bartsch, R.A., J. Phys. Org. Chem., 2005, vol. 18, p. 1107.

    Article  CAS  Google Scholar 

  3. McKie, R., Murphy, J.A., Park, S.R., Spicer, M.D., and Zhou, S., Angew. Chem., Int. Ed., 2007, vol. 46, p. 6525.

    Article  CAS  Google Scholar 

  4. Maltceva, O.V., Chizhova, N.V., Kumeev, R.S., and Mamardashvili, N.Z., Macroheterocycles, 2017, vol. 10, p.68.

    Article  CAS  Google Scholar 

  5. Jovené, C., Marrot, J., Jasmin, J.-P., Chugunova, E., and Goumont, R., Eur. J. Org. Chem., 2016, no. 23, p. 4084.

    Article  CAS  Google Scholar 

  6. Chugunova, E.A., Akylbekov, N.I., Appazov, N.O., Makhrus, E.M., and Burilov, A.R., Russ. J. Org. Chem., 2016, vol. 52, p.920.

    Article  CAS  Google Scholar 

  7. Bogdanov, A.V., Zaripova, I.F., Voloshina, A.D., Strobykina, A.S., Kulik, N.V., Bukharov, S.V., Voronina, J.K., Khamatgalimov, A.R., and Mironov, V.F., Monatsh. Chem., 2018, vol. 149, p.111.

    Article  CAS  Google Scholar 

  8. Gazizov, A.S., Kharitonova, N.I., Smolobochkin, A.V., Syakaev, V.V., Burilov, A.R., and Pudovik, M.A., Monatsh. Chem., 2015, vol. 146, p. 1845.

    Article  CAS  Google Scholar 

  9. Bogdanov, A.V., Musin, L.I., and Mironov, V.F., Arkivoc, 2015, part (vi), p.362.

    Google Scholar 

  10. Bruyneel, F., Letondor, C., Bastürk, B., Gualandi, A., Pordea, A., Stoeckli-Evans, H., and Neier, R., Adv. Synth. Catal., 2012, vol. 354, p.428.

    Article  CAS  Google Scholar 

  11. Blangy, V., Heiss, C., Khlebnikov, V., Letondor, C., Stoeckli-Evans, H., and Neier, R., Angew. Chem., Int. Ed., 2008, vol. 48, p. 1688.

    Article  CAS  Google Scholar 

  12. Journot, G., Neier, R., and Stoeckli-Evans, H., Acta Crystallogr., Sect. C, 2014, vol. 70, p.644.

    Article  CAS  Google Scholar 

  13. Kubik, S., Reyheller, C., and Stüwe, S., J. Inclusion Phenom. Macrocyclic Chem., 2005, vol. 52, p.137.

    Article  CAS  Google Scholar 

  14. Journot, G., Letondor, C., Neier, R., Stoeckli-Evans, H., Savoia, D., and Gualandi, A., Chem. Eur. J., 2010, vol. 16, p. 4224.

    Article  CAS  PubMed  Google Scholar 

  15. Smolobochkin, A.V., Gazizov, A.S., Burilov, A.R., and Pudovik, M.A., Russ. J. Gen. Chem., 2015, vol. 85, p.517.

    Article  CAS  Google Scholar 

  16. Gazizov, A.S., Smolobochkin, A.V., Burilov, A.R., and Pudovik, M.A., Chem. Heterocycl. Compd., 2014, vol. 50, no. 5, p.707.

    Article  CAS  Google Scholar 

  17. Gazizov, A.S., Kharitonova, N.I., Smolobochkin, A.V., Syakaev, V.V., Burilov, A.R., and Pudovik, M.A., Monatsh. Chem., 2015, vol. 146, p. 1845.

    Article  CAS  Google Scholar 

  18. Smolobochkin, A.V., Gazizov, A.S., Burilov, A.R., and Pudovik, M.A., Russ. J. Gen. Chem., 2015, vol. 85, p. 1779.

    Article  CAS  Google Scholar 

  19. Smolobochkin, A.V., Gazizov, A.S., Burilov, A.R., and Pudovik, M.A., Russ. Chem. Bull., Int. Ed., 2016, vol. 65, no. 5, p. 1377.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Akademika Arbuzova 8, Kazan, 420088 Tatarstan, Russia

    A. V. Smolobochkin, A. S. Gazizov, A. R. Burilov & M. A. Pudovik

Authors
  1. A. V. Smolobochkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Gazizov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. R. Burilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. A. Pudovik
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Smolobochkin.

Additional information

Original Russian Text © A.V. Smolobochkin, A.S. Gazizov, A.R. Burilov, M.A. Pudovik, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 9, pp. 1414–1416.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Smolobochkin, A.V., Gazizov, A.S., Burilov, A.R. et al. Synthesis of Macroheterocycles by Reaction of N,N′-(1,4-Phenylene)bis[N′-(4,4-diethoxybutyl)urea] with Resorcinol and Its Derivatives. Russ J Org Chem 54, 1432–1434 (2018). https://doi.org/10.1134/S1070428018090300

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018090300

Search

Navigation