Skip to main content
SpringerLink
Log in

The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides with sulfonyl chlorides and acetyl and benzoyl chlorides is accompanied by the Dimroth rearrangement and proceeds regiospecifically with the formation of 5-arylamino-2-sulfonyl(acyl)-1,2,3-triazoles. The reaction mechanism was confirmed by the synthesis of the target products via the reaction of 5-arylamino-1,2,3-triazole-4-carbothioamides with sulfonyl and acyl chlorides.

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. (a) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905. (b) Agalave, S. G.; Maujan, S. R.; Pore, V. S. Chem.–Asian J. 2011, 6, 2696. (c) Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278. (d) Coleman, P. J.; Gotter, A. L.; Herring, W. J.; Winrow, C. J.; Renger, J. J. Annu. Rev. Pharmacol. Toxicol. 2017, 57, 509. (e) Lai, Q.; Liu, Q.; Zhao, K.; Shan, C.; Wojtas, L.; Zheng, Q.; Shi, X.; Song, Z. Chem. Commun. 2019, 55, 4603. (f) Raheem, I. T.; Breslin, M. J.; Bruno, J.; Cabalu, T. D.; Cooke, A.; Cox, C. D.; Cui, D. H.; Garson, S.; Gotter, A. L.; Fox, S. V.; Harrell, C. M.; Kuduk, S. D.; Lemaire, W.; Prueksaritanont, T.; Renger, J. J.; Stump, C.; Tannenbaum, P. L.; Williams, P. D.; Winrow, C. J.; Coleman, P. J. Bioorg. Med. Chem. Lett. 2015, 25, 444.

  2. (a) Hopkins, C. R. ACS Chem. Neurosci. 2012, 3, 647. (b) Sun, H.; Kennedy, W. P.; Wilbraham, D.; Lewis, N.; Calder, N.; Li, X.; Ma, J.; Yee, K. L.; Ermlich, S.; Mangin, E.; Lines, C.; Rosen, L.; Chodakewitz, J.; Murphy, G. M. Sleep 2013, 36, 259.

  3. Hoyer, D.; Allen, A.; Jacobson, L. H. Br. J. Clin. Pharmacol. 2020, 86, 244.

    Article  Google Scholar 

  4. (a) Gentile, T. A.; Simmons, S. J.; Barker, D. J.; Shaw, J. K.; España, R. A.; Muschamp, J. W. Addict. Biol. 2017, 23, 247. (b) De Boer, P.; Drevets, W. C.; Rofael, H.; van der Ark, P.; Kent, J. M.; Kezic, I.; Parapatics, S.; Dorffner, G.; van Gerven, J.; Beneš, H.; Keicher, C.; Jahn, H.; Seiden, D. J.; Luthringer, R. J. Psychopharmacol. 2018, 32, 668.

  5. Bakulev, V.; Dehaen, W.; Beryozkina, T. Top. Heterocycl. Chem. 2015, 40, 1.

    CAS  Google Scholar 

  6. (a) Gataullin, R. R.; Zileeva, Z. R.; Maksimova, M. A.; Zainullina, L. F.; Vakhitova, Y. V. J. Heterocycl. Chem. 2020, 57, 1236. (b) Zhong, B.; Cai, X.; Chennamaneni, S.; Yi, X.; Liu, L.; Pink, J. J.; Dowlati, A.; Xu, Y.; Zhou, A.; Su, B. Eur. J. Med. Chem. 2012, 47, 432.

  7. Zheng, P.-C.; Cheng, J.; Su, S.; Jin, Z.; Wang, Y.-H.; Yang, S.; Jin, L.-H.; Song, B.-A.; Chi, Y. R. Chem.–Eur. J. 2015, 21, 9984.

    Article  CAS  Google Scholar 

  8. Füsslein, M.; Wroblowsky, H.-J.; Kübbeler, S.; Hager, D.; Kausch-Busies, N.; Andree, R.; Jansen, J.-R.; Schwarz, H.-G.; Portz, D.; Ilg, K.; Malsam, O.; Eilmus, S.; Lösel, P.; Herrmann, S.; Becker, A.; Voerste, A.; Göergens, U.; Lishchynskyi, A.; Turberg, A. WO Patent 2018083288 A1 20180511.

  9. Witherington, J.; Abberley, L.; Bellenie, B. R.; Boatman, R.; Collis, K.; Dean, D. K.; Gaiba, A.; King, N. P.; Shuker, N.; Steadman, J. G. A.; Takle, A. K.; Sanger, G.; Butler, S.; McKay, F.; Muir, A.; Winborn, K.; Ward, R. W.; Heightman, T. D. Bioorg. Med. Chem. Lett. 2009, 19, 684.

    Article  CAS  Google Scholar 

  10. (a) Beryozkina, T. V.; Efimov, I. V.; Fabian, W. M. F.; Beliaev, N. A.; Slepukhin, P. A.; Isenov, M. L.; Dehaen, W.; Lubec, G.; Eltsov, O. S.; Fan, Z.; Thomas, J.; Bakulev, V. A. Tetrahedron 2015, 71, 6189. (b) Bakulev, V. A.; Beryozkina, T. V. Chem. Heterocycl. Compd. 2016, 52, 4. [Khim. Geterotsikl. Soedin. 2016, 52, 4.] (c) L’abbe, G.; Mahy, M.; Bollyn, M.; Germain, G.; Scheefer, G. Bull. Soc. Chim. Belg. 1983, 92, 881.

  11. (a) Beryozkina, T. V.; Filimonov, V. O.; Dianova, L. N.; Slepukhin, P. A.; Mazur, D. M.; Pospelova, T. A.; Bakulev, V. A. Chem. Heterocycl. Compd. 2019, 55, 547. [Khim. Geterotsikl. Soedin. 2019, 55, 547.] (b) Bakulev, V. A.; Tarasov, E. V.; Morzherin, Yu. Yu.; Luyten, I.; Toppet, S.; Dehaen, W. Tetrahedron 1998, 54, 8501.

  12. Ilkin, V. G.; Dianova, L. N.; Bakulev, V. A.; Berseneva, V. S.; Saveliev, D. A.; Beryozkina, T. V. Chem. Heterocycl. Compd. 2020, 56, 1335. [Khim. Geterotsikl. Soedin. 2020, 56, 1335] Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

  13. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

Download references

This work was supported by the Russian Foundation for Basic Research (grant 18-03-00715).

Author information

Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St, Yekaterinburg, 620002, Russia

    Lidiya N. Dianova, Tetyana V. Beryozkina, Valeriy O. Filimonov & Vasiliy А. Bakulev

  2. State Key Laboratory of Elemento organic Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China

    Zhijin Fan

  3. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St, Yekaterinburg, 620108, Russia

    Pavel А. Slepukhin

Authors
  1. Lidiya N. Dianova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tetyana V. Beryozkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Valeriy O. Filimonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhijin Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Pavel А. Slepukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Vasiliy А. Bakulev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vasiliy А. Bakulev.

Additional information

Dedicated to Professor A.F. Khlebnikov on the occasion of his 70th birthday

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1341–1347

Supplementary Information

ESM 1

(PDF 1829 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dianova, L.N., Beryozkina, T.V., Filimonov, V.O. et al. The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides. Chem Heterocycl Comp 56, 1341–1347 (2020). https://doi.org/10.1007/s10593-020-02820-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02820-3

Keywords

Search

Navigation