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.

About the authors

D. I. Antonov

Perm State University

Perm, Russia

M. V. Dmitriev

Perm State University

Perm, Russia

I. A. Kuchumov

Perm State University

Perm, Russia

A. N. Maslivets

Perm State University

Email: koh2@psu.ru
Perm, Russia

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

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