Skip to main content
Log in

Synthesis of novel macrocyclic and heterocyclic taurine derivatives based on the reaction of sodium 2-[(4,4-diethoxybutyl)amino]ethanesulfonate with phenols

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A Correction to this article was published on 01 August 2020

This article has been updated

An approach to the synthesis of novel macrocyclic and heterocyclic taurine derivatives based on the reaction of sodium 2-[(4,4-diethoxybutyl)amino]ethanesulfonate with phenols in the presence of trifluoroacetic acid has been developed. The structures of the obtained products are confirmed by spectral data.

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

Change history

  • 23 September 2020

    To the article ���Synthesis of novel macrocyclic and heterocyclic taurine derivatives based on the reaction of sodium 2-[(4,4-diethoxybutyl)amino]ethanesulfonate with phenols��� by Andrey V. Smolobochkin, Lola Zh. Yakhshilikova, Almir S. Gazinov, Liliya I. Vagapova, Alexander R. Burilov, Michael A. Pudovik

References

  1. Ananikov, V. P.; Khemchyan, L. L.; Ivanova, Y. V.; Bukhtiyarov, V. I.; Sorokin, A. M.; Prosvirin, I. P.; Vatsadze, S. Z.; Medved'ko, A. V.; Nuriev, V. N.; Dilman, A. D.; Levin, V. V.; Koptyug, I. V.; Kovtunov, K. V.; Zhivonitko, V. V.; Likholobov, V. A.; Romanenko, A. V.; Simonov, P. A.; Nenajdenko, V. G.; Shmatova, O. I.; Muzalevskiy, V. M.; Nechaev, M. S.; Asachenko, A. F.; Morozov, O. S.; Dzhevakov, P. B.; Osipov, S. N.; Vorobyeva, D. V.; Topchiy, M. A. Zotova, M. A.; Ponomarenko, S. A.; Borshchev, O. V.; Luponosov, Y. N.; Rempel, A. A.; Valeeva, A. A.; Stakheev, A. Y.; Turova, O. V.; Mashkovsky, I. S.; Sysolyatin, S. V.; Malykhin, V. V.; Bukhtiyarova, G. A.; Terent'ev, A. O.; Krylov, I. B. Russ. Chem. Rev. 2014, 83, 885. [Usp. Khim. 2014, 83, 885.]

    Google Scholar 

  2. Schuller-Levis, G. B.; Park, E. FEMS Microbiol. Lett. 2003, 226, 195.

    Article  CAS  Google Scholar 

  3. (a) Brosnan, J. T.; Brosnan, M. E. J. Nutr. 2006, 136, 1636S. (b) Huxtable, R. J. Physiol. Rev. 1992, 72, 101. (c) Marcinkiewicz, J.; Kontny, E. Amino Acids 2014, 46, 7.

  4. (a) Faul, M.; Larsen, R.; Levinson, A.; Tedrow, J.; Vounatsos, F. J. Org. Chem. 2013, 78, 1655. (b) McKinnell, R. M.; Armstrong, S. R.; Beattie, D. T.; Choi, S.-K.; Fatheree, P. R.; Gendron, R. A. L.; Goldblum, A.; Humphrey, P. P.; Long, D. D.; Marquess, D. G.; Shaw, J. P.; Smith, J. A. M.; Turner, S. D.; Vickery, R. G. J. Med. Chem. 2009, 52, 5330. (с) Al-Riyami, L.; Pineda, M. A.; Rzepecka, J.; Huggan, J. K.; Khalaf, A. I.; Suckling, C. J.; Scott, F. J.; Rodgers, D. T.; Harnett, M. M.; Harnett, W. J. Med. Chem. 2013, 56, 9982. b Bagautdinova, R. Kh.; Vagapova, L. I.; Smolobochkin, A. V.; Gaziziov, A. S.; Burilov, A. R.; Pudovik, M. A.; Voloshina, A. D. Mendeleev Commun. 2019, 29, 686.

  5. Kosswig, K. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA, 2000, p. 1.

  6. (a) Hu, L.; Zhu, H.; Du, D.-M.; Xu, J. J. Org. Chem. 2007, 72, 4543. (b) Xu, J. Tetrahedron: Asymmetry 2002, 13, 1129. (c) Chen, N.; Zhu, M.; Zhang, W.; Du, D.-M.; Xu, J. Amino Acids 2009, 37, 309.

  7. Chen, N.; Jia, W.; Xu, J. Eur. J. Org. Chem. 2009, 5841.

  8. Koller, W.; Linkies, A.; Rehling, H.; Reuschling, D. Tetrahedron Lett. 1983, 24, 2131.

    Article  CAS  Google Scholar 

  9. (a) Stipanuk, M. H. Annu. Rev. Nutr. 1986, 6, 179. (b) Soboleva, A. V.; Krasnoshtanova, A. A.; Krylov, I. A. Appl. Biochem. Microbiol. 2004, 40, 236.

  10. (a) Xu, J.; Xu, S.; Zhang, Q. Heteroat. Chem. 2005, 16, 466. (b) Higashiura, K.; Ienaga, K. J. Org. Chem. 1992, 57, 764. (c) Huang, J.; Du, D.-M.; Xu, J. Synthesis 2006, 315. (d) Huang, J.; Wang, F.; Du, D.-M.; Xu, J. Synthesis 2005, 2122.

  11. (a) Philippossian, G.; Welti, D. H.; Fumeaux, R.; Richli, U.; Anantharaman, K. J. Labelled Compd. Radiopharm. 1989, 27, 1267. (b) Marvel, C. S.; Bailey, C. F. Org. Synth. 1938, 18, 77.

  12. Bondareva, O. M.; Lopatik, D. V.; Kuvaeva, Z. I.; Vinokurova, L. G.; Markovich, M. M.; Prokopovich, I. P. Pharm. Chem. J. 2008, 42, 142.

    Article  CAS  Google Scholar 

  13. Cordero, F. M.; Cacciarini, M.; Machetti, F.; De Sarlo, F. Eur. J. Org. Chem. 2002, 1407.

  14. (a) García-Gallego, S.; Rodríguez, J. S.; Jiménez, J. L.; Cangiotti, M.; Ottaviani, M. F.; Muñoz-Fernández, M. Á.; Gómez, R.; de la Mata, F. J. Dalton Trans. 2012, 41, 6488. (b) De, S.; Groaz, E.; Margamuljana, L.; Abramov, M.; Marlière, P.; Herdewijn, P. Org. Biomol. Chem. 2015, 13, 3950. (c) García-Gallego, S.; Serramía, M. J.; Arnaiz, E.; Díaz, L.; Muñoz-Fernández, M. A.; Gómez-Sal, P.; Ottaviani, M. F.; Gómez, R.; de la Mata, F. J. Eur. J. Inorg. Chem. 2011, 1657. (d) Liang, H.-C.; Das, S. K.; Galvan, J. R.; Sato, S. M.; Zhang, Y.; Zakharov, L. N.; Rheingold, A. L. Green Chem. 2005, 7, 410.

  15. Gazizov, A. S.; Smolobochkin, A. V.; Anikina, E. A.; Strelnik, A. G.; Burilov, A. R.; Pudovik, M. A. Synlett 2018, 467.

Download references

This work was financially supported by the Russian Foundation for Basic Research and the Government of the Republic of Tatarstan (project No. 18-43-160004).

The authors are grateful to the Collective Spectro-Analytical Center for Physicochemical Studies of the Structure, Properties and Composition of Substances and Materials of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences” for technical support of the studies.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Andrey V. Smolobochkin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 888–891

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Smolobochkin, A.V., Yakhshilikova, L.Z., Gazinov, A.S. et al. Synthesis of novel macrocyclic and heterocyclic taurine derivatives based on the reaction of sodium 2-[(4,4-diethoxybutyl)amino]ethanesulfonate with phenols. Chem Heterocycl Comp 56, 888–891 (2020). https://doi.org/10.1007/s10593-020-02746-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02746-w

Keywords

Navigation