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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 12, pp 1590–1592 | Cite as

Formation of 4-aroylhydrazono-2-methyl- 5-oxo-1-phenyl-3-phenylaminooxalyl-pyrrolidine-2-carboxylates

  • V. L. GeinEmail author
  • R. O. Dyrenkov
  • N. A. Kornienko
  • M. I. Vakhrin
  • G. A Veikhman
  • P. A. Slepukhin
Letters to the Editor

The reaction of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with benzoic acid hydrazide has previously been studied, and the structure of the compound obtained was confirmed by X-ray structural analysis [1].

We have for the first time studied the reaction of a pyrrole-2,3-dione ring annelated to a pyrroline ring (compounds 1, 2) with benzoic acid hydrazides. The reaction with said reagents proceeds when refluxed in acetonitrile over 3-5 min to give the 4-aroylhydrazono-2-methyl-5-oxo-1-phenyl-3-phenylaminooxalylpyrrolidine-2-carboxylates 3-6.

The compounds 3-6 obtained are yellow, crystalline substances soluble in DMF and DMSO, but also in less polar organic solvents when heated.

The IR spectra of compounds 3-6 show stretching bands for the N–H bonds at 3290-3355 cm-1, ester carbonyl group at 1724-1750, amide carbonyl groups at 1684-1705, and ketonic carbonyl group at 1600-1610 cm-1.

The 1 H NMR spectra of compounds 3-6show signals for the aliphatic and aromatic protons and...

Keywords

aromatic acid hydrazides pyrroles pyrrolines pyrrolo[3,4-b]pyrrole-2,3,6-triones pyrrolidine-2-carboxylates 

References

  1. 1.
    I. V. Mashevskaya, M. L. Klinchina, I. G. Mokrushin, Z. G. Aliev, and A. N. Maslivets, Zh. Org. Khim., 45, 1878 (2009).Google Scholar
  2. 2.
    G. M. Sheldrick, Acta Cryst., A64, 112 (2008).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • V. L. Gein
    • 1
    Email author
  • R. O. Dyrenkov
    • 1
  • N. A. Kornienko
    • 1
  • M. I. Vakhrin
    • 1
  • G. A Veikhman
    • 1
  • P. A. Slepukhin
    • 2
  1. 1.Perm State Pharmaceutical AcademyPermRussia
  2. 2.I. Ya. Postovsky Institute of Organic Synthesis22 Kovalevky St., 20 Academic St., Ural Branch of the Russian Academy of SciencesYekaterinburgRussia

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