Skip to main content
SpringerLink
Log in

A one-pot thiomethylation of pyrrole and indoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

C(sp2)H functionalization of pyrrole, indole, indolyl-3-acetic acid (heteroauxin), and 2-amino-3-(indol-3yl)propionic acid (tryptophan) was carried out via a one-pot C-thiomethylation with formaldehyde and mercaptans in pyridine which simultaneously played the role of a catalyst and solvent. The possibility of the synthesis of structurally diverse sulfanyl methylindoles depending on the nature of the reagents was demonstrated.

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

Figure 1
Figure 2

Similar content being viewed by others

References

  1. Fatemeh, G.; Sajjad, M.; Niloufar, R.; Neda, S.; Leila, S.; Khadijeh, M. J. Neurology 2022, 269, 205.

    Article  CAS  Google Scholar 

  2. Wang, L.; Pan, Y.; Ye, C.; Guo, L.; Luo, S.; Dai, S.; Chen, N.; Wang, E. Neurosci. Biobehav. Rev. 2021, 131, 489.

    Article  CAS  PubMed  Google Scholar 

  3. Johnson, H. E.; Crosby, D. G. Org. Synth. 1964, 44, 64.

    Article  CAS  Google Scholar 

  4. Shibaeva, T. G.; Markovskaya, E. F.; Mamaev, A. V. Zhurn. Obsh. Biologii 2017, 78, 46.

    Google Scholar 

  5. Knyaz'kin, I. V. Uspekhi gerontol. 2007, 21, 74.

    Google Scholar 

  6. Lucas, S. Headache 2016, 56, 436. DOI: https://doi.org/10.1111/head.12769PMID. 26865183

    Article  PubMed  Google Scholar 

  7. Tabet, N.; Naji, T.; Feldman, H. Cochrane Database Systematic Review 2002, 2, CD003673.

  8. Azmitia, E. C. Handbook Behavioral-Neurosciences; 2020, Vol. 31, p. 3.

  9. Dürk, T.; Panther, E.; Müller, T.; Sorichter, S.; Ferrari, D.; Pizzirani, C.; Di Virgilio, F.; Myrtek, D.; Norgauer, J.; Idzko, M. Int. Immunol. 2005, 17, 599.

    Article  PubMed  Google Scholar 

  10. Zhang, M-Z.; Chen, Q.; Yang, G.-F. Eur. J. Med. Chem. 2015, 89, 421.

    Article  CAS  PubMed  Google Scholar 

  11. Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Ananikov, V. P.; Khemchyan, L. L.; Ivanova, Yu. V.; Bukhtivarov, V. I.; Sorokin, A. M.; Prosvirin, A. M.; 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, Yu. N.; Rempel, A. A.; Valeeva, A. A.; Stakheev, A. Yu.; Turova, O. V.; Mashkovsky, I. S.; Sysolyatin, S. V.; Malykhin, V. V.; Bukhtivarova, G. G.; Terent'ev, A. O.; Krylov, I. B. Russ. Chem. Rev. 2014, 83, 885.

    Article  Google Scholar 

  13. Rakitin, O. A. Chem. Heterocycl. Compd. 2020, 56, 837.

    Article  CAS  Google Scholar 

  14. Sharipov, M. Yu.; Krylov, I. B.; Karpov, I. D.; Vasilkova, O. V.; Oleksiienko, A. M. V.; Terent'ev, A. O. Chem. Heterocycl. Compd. 2021, 57, 531.

    Article  CAS  Google Scholar 

  15. Kuzu, E.; Kuzu, B. Chem. Heterocycl. Compd. 2023, 59, 80.

    Article  CAS  Google Scholar 

  16. Kiamehr, M.; Khademi, F.; Jafari, B.; Langer, P. Chem. Heterocycl. Compd. 2020, 56, 392.

    Article  CAS  Google Scholar 

  17. Grozav, A. N.; Fedoriv, M. Z.; Chornous, V. A.; Palamar, A. A.; Bratenko, M. K.; Vovk, M. V. Chem. Heterocycl. Compd. 2019, 55, 435.

    Article  CAS  Google Scholar 

  18. De Lucchi, O.; Miotti, U.; Modena, G. ChemInform 1992, 23, 03-294.

    Google Scholar 

  19. Kim, I. T.; Elsenbaumer, R. L. Tetrahedron Lett. 1998, 39, 1087.

    Article  CAS  Google Scholar 

  20. Kreutzkamp, N.; Oei, H. Y.; Peschel, H. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1971, 304, 649.

    Article  CAS  PubMed  Google Scholar 

  21. Nirogi, R.; Reddy, T.; Konda, J.; Reballi, V.; Gudla, P.; Kambhampati, R.; Khagga, M. Pharma Chem. 2012, 4, 1567.

    CAS  Google Scholar 

  22. Thielmann, T.; Güntert, M.; Köpsel, M.; Werkhoff, P. Tetrahedron Lett. 1989, 30, 4507.

    Article  CAS  Google Scholar 

  23. Akhmetova, V. R.; Akhmadiev, N. S.; Starikova, Z. A.; Tulyabaev, A. R.; Mescheryakova, E. S.; Ibragimov, A. G. Tetrahedron 2015, 71, 7722.

    Article  CAS  Google Scholar 

  24. Gordon, A.; Ford, R. Sputnik khimika (The Chemist's Companion [Russian translation); Moscow: Mir, 1976, p. 73.

    Google Scholar 

  25. Unger, T. A. Pesticide Synthesis Handbook; 1996, p. 458.

  26. Almeida, M. C.; Resende, D. I. S. P.; da Costa, P. M.; Pinto, M. M. M.; Sousa, E. Eur. J. Med. Chem. 2021, 209, 112945

    Article  CAS  PubMed  Google Scholar 

  27. Voskressensky, L. G.; Borisova, T. N.; Babakhanova, M. L.; Chervyakova, T. M.; Titov, A. A.; Novikov, R. A.; Toze, F.; Dang, T. A.; Varlamov, A. V. Chem. Heterocycl. Compd. 2015, 51, 639.

    Article  CAS  Google Scholar 

  28. Grant, N.; Ward, M. F.; Jaspars, M.; Harrison, W. T. A. Acta Crystallogr., Sect. E: Struct. Rep. Online 2001, E57, o697.

  29. Conde-Caprace, G.; Collin, J. E. Org. Mass Spectrom. 1972, 6, 415.

    Article  CAS  Google Scholar 

  30. Maciejewska, D.; Szpakowska, I.; Wolska, I.; Niemyjska, M.; Mascini, M.; Maj-Żurawska, M. Bioelectrochemistry 2006, 69, 1.

    Article  CAS  PubMed  Google Scholar 

  31. Jagtap, R. M.; Thorat, S. H.; Gonnade, R. G.; Khan, A. A.; Pardeshi, S. K. New J. Chem. 2018, 42, 1078.

    Article  CAS  Google Scholar 

Download references

Acknowledgement

The work was carried out within the framework of the State Assignment FMRS-2022-0079.

Structural studies of compounds 3a,b, 4a,b, 5a–c, 6a–e, 7a,b, 8, 9 were carried out at the Regional Center for Collective Use “Agidel”, at the Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave, Ufa, 450075, Russia

    Vnira R. Akhmetova, Danil V. Leont’ev, El’mira M. Galimova & Ekaterina S. Mescheryakova

Authors
  1. Vnira R. Akhmetova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Danil V. Leont’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. El’mira M. Galimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ekaterina S. Mescheryakova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vnira R. Akhmetova.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(11/12), 826–832

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 930 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Akhmetova, V.R., Leont’ev, D.V., Galimova, E.M. et al. A one-pot thiomethylation of pyrrole and indoles. Chem Heterocycl Comp 59, 826–832 (2023). https://doi.org/10.1007/s10593-024-03278-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-024-03278-3

Keywords

Search

Navigation