Skip to main content
Log in

Recyclization of 5-Aryl-1H-pyrrole-2,3-diones with Amidoximes. Synthesis of Enamines Containing a 1,2,4-Oxadiazole Fragment

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

Abstract

5-Aryl-1H-pyrrole-2,3-diones reacted with amidoximes to give enamines containing a 1,2,4-oxadi­azole fragment that are potential precursors to novel 1H-pyrrole-2,3-diones. The described reaction is the first example of recyclization of 4-unsubstitued 5-aryl-1H-pyrrole-2,3-diones by the action of 1,4-binucleophiles.

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.

Scheme
Fig. 1.

REFERENCES

  1. Bethge, K., Pertz, H.H., and Rehse, K., Arch. Pharm. (Weinheim, Ger.), 2005, vol. 338, p. 78. https://doi.org/10.1002/ardp.200400927

    Article  CAS  Google Scholar 

  2. dos Santos Filho, J.M., Moreira, D.R.M., de Simone, C.A., Ferreira, R.S., McKerrow, J.H., Meira, C.S., Guimaraes, E.T., and Soares, M.B.P., Bioorg. Med. Chem., 2012, vol. 20, p. 6423. https://doi.org/10.1016/j.bmc.2012.08.047

    Article  CAS  PubMed  Google Scholar 

  3. Qiu, H., Ali, Z., Bender, A., Caldwell, R., Chen, Y.-Y., Fang, Z., Gardberg, A., Glaser, N., Goettsche, A., Goutopoulos, A., Grenningloh, R., Hanschke, B., Head, J., Johnson, T., Jones, C., Jones, R., Kulkarni, S., Maurer, C., Morandi, F., Neagu, C., Poetzsch, S., Potnick, J., Schmidt, R., Roe, K., Follis, A.V., Wing, C., Zhu, X., and Sherer, B., Bioorg. Med. Chem., 2021, vol. 40, article ID 116163. https://doi.org/10.1016/j.bmc.2021.116163

  4. Moniot, S., Forgione, M., Lucidi, A., Hailu, G.S., Nebbioso, A., Carafa, V., Baratta, F., Altucci, L., Giacché, N., Passeri, D., Pellicciari, R., Mai, A., Steegborn, C., and Rotili, D., J. Med. Chem., 2017, vol. 60, p. 2344. https://doi.org/10.1021/acs.jmedchem.6b01609

    Article  CAS  PubMed  Google Scholar 

  5. Ozcan, S., Kazi, A., Marsilio, F., Fang, B., Guida, W.C., Koomen, J., Lawrence, H.R., and Sebti, S.M., J. Med. Chem., 2013, vol. 56, p. 3783. https://doi.org/10.1021/jm400221d

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Santos-Filho, J.M., de Lima, J.G., Leite, L.F.C.C., Ximenes, Ε.A., da Silva, J.Β.P., Lima, P.C., and Pitta, I.R., Heterocycl. Commun., 2005, vol. 11, p. 29. https://doi.org/10.1515/HC.2005.11.1.29

    Article  CAS  Google Scholar 

  7. Cobas, A., Guitian, E., and Castedo, L., J. Org. Chem., 1993, vol. 58, p. 3113. https://doi.org/10.1021/jo00063a034

    Article  CAS  Google Scholar 

  8. Gangloff, A.R., Litvak, J., Shelton, E.J., Sperandio, D., Wang, V.R., and Rice, K.D., Tetrahedron Lett., 2001, vol. 42, p. 1441. https://doi.org/10.1016/S0040-4039(00)02288-7

    Article  CAS  Google Scholar 

  9. CrysAlisPro. Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET).

  10. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  11. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  12. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

Download references

Funding

This study was performed under financial support by the Russian Foundation for Basic Research (project nos. 20-33-90264 and 20-43-596008), Perm Krai, and Ministry of Science and Higher Education of the Russian Federation (project no. FSNF-2023-0004).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. N. Maslivets.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Antonov, D.I., Dmitriev, M.V., Kuchumov, I.A. et al. Recyclization of 5-Aryl-1H-pyrrole-2,3-diones with Amidoximes. Synthesis of Enamines Containing a 1,2,4-Oxadiazole Fragment. Russ J Org Chem 60, 387–390 (2024). https://doi.org/10.1134/S1070428024030023

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428024030023

Keywords:

Navigation