Recyclization of 5-Aryl-1H-pyrrole-2,3-diones under the Action of Amidoximes. Synthesis of Enamines with a 1,2,4-Oxadiazole Moiety

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Abstract

5-Aryl-1Н-pyrrole-2,3-diones react with amidoximes to form enamines with a 1,2,4-oxadiazole fragment, which are potential precursors of a new type of 1Н-pyrrole-2,3-diones. The described reaction is the first example of the recyclization of 4-unsubstituted 5-aryl-1H-pyrrole-2,3-diones under action of 1,4-binucleophilic reagent.

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About the authors

Dmitry I. Antonov

Perm State University

Author for correspondence.
Email: koh2@psu.ru
ORCID iD: 0000-0002-7101-1351
Russian Federation, 15, Bukirev St., Perm, 614068

Maxim V. Dmitriev

Perm State University

Email: koh2@psu.ru
ORCID iD: 0000-0002-8817-0543
Russian Federation, 15, Bukirev St., Perm, 614068

Ilya A. Kuchumov

Perm State University

Email: koh2@psu.ru
ORCID iD: 0000-0002-4511-7451
Russian Federation, 15, Bukirev St., Perm, 614068

Andrey N. Maslivets

Perm State University

Email: koh2@psu.ru
ORCID iD: 0000-0001-7148-4450
Russian Federation, 15, Bukirev St., Perm, 614068

References

  1. Bethge K., Pertz H.H., Rehse K. Arch. Pharm.: Int. J. Pharm. Med. Chem. 2005, 338, 78–86. doi: 10.1016/j.bmc.2021.116163
  2. dos Santos Filho J.M., Moreira D.R.M., de Simone C.A., Ferreira R.S., McKerrow J.H., Meira C.S., Soares M.B.P. Bioorg. Med. Chem. 2012, 20, 6423–6433. doi: 10.1016/j.bmc.2012.08.047
  3. Qiu H., Ali Z., Bender A., Caldwell R., Chen Y.Y., Fang Z., Sherer B. Bioorg. Med. Chem. 2021, 40, 161–163. doi: 10.1016/j.bmc.2021.116163
  4. Moniot S., Forgione M., Lucidi A., Hailu G.S., Nebbioso A., Carafa V., Rotili D. J. Med. Chem. 2017, 60, 2344–2360. doi: 10.1021/acs.jmedchem.6b01609
  5. Ozcan S., Kazi A., Marsilio F., Fang B., Guida W.C., Koomen J., Sebti S.M. J. Med. Chem. 2013, 56, 3783–3805. doi: 10.1021/jm400221d
  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. Heterocycl. Commun. 2005, 11, 29–36. doi: 10.1515/HC.2005.11.1.29
  7. Cobas A., Guitian E., Casted L. J. Org. Chem. 1993, 58, 3113–3117. doi: 10.1021/jo00063a034
  8. Gangloff A.R., Litvak J., Shelton E.J., Sperandio D., Wang V.R., Rice K.D. Tetrahedron Lett. 2001, 42, 1441–1443. doi: 10.1016/S0040-4039(00)02288-7
  9. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET)
  10. Sheldrick G.M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112–122. doi: 10.1107/S0108767307043930
  11. Sheldrick G.M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71, 3–8. doi: 10.1107/S2053229614024218
  12. Dolomanov O.V., Bourhis L.J., Gildea R.J, Howard J.A.K., Puschmann H. J. Appl. Cryst. 2009, 42, 339–341. doi: 10.1107/S0021889808042726

Supplementary files

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2. Scheme

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3. Fig. General view of the molecule of compound 3a from PCA data in the representation of atoms by thermal vibration ellipsoids with 30% probability.

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