Chemistry of Heterocyclic Compounds

, Volume 48, Issue 6, pp 972–973 | Cite as

Formation of 3-[2-oxo-2-(2-heteryl)ethylidene]-3,4-dihydroquinoxalin-2(1H)-ones in the reaction of 5-aryl-4-heteroyl-3-hydroxy-1-thiazolyl-3-pyrrolin-2-ones with o-phenylenediamine

  • V. L. Gein
  • M. A. Mar’yasov
  • T. A. Silina

We have previously shown that the reaction of 1,5-diaryl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones with o-phenylenediamine gives dihydropyrrolo[2,3-b]quinoxalines [1]. A similar process accompanied by dehydrogenation takes place upon fusing 1,5-diaryl-3-hydroxy-4-methylsulfonyl-3-pyrrolin-2-ones with o-phenylenediamine [2]. In the case of the reaction of 1,5-diaryl-4-tert-butoxycarbonyltetrahydropyrrole-2,3-diones with o-phenylenediamine the single reaction product is a 1,2-diaryl-3,10-dioxo-1,2,4,9-tetrahydro-pyrrolo[3,4-b][1,5]benzodiazepines [3].

With the aim of further examining the properties of the substituted pyrrole-2,3-diones, we have studied the reaction of 5-aryl-4-heteroyl-3-hydroxy-1-thiazolyl-3-pyrrolin-2-ones with o-phenylenediamine. The starting compounds were prepared according to the previously reported method [4].

Refluxing compounds 1, 2 with o-phenylenediamine in glacial acetic acid for 3 h gives only 3-[2-oxo-2-(2-heteryl)ethylidene]-3,4-dihydroquinoxalin-2(1H)...


5-aryl-4-heteroyl-3-hydroxy-1-thiazolyl-3-pyrrolin-2-ones binucleophiles o-phenylene-diamine quinoxalones 


  1. 1.
    W. R. Vaughan and R. C. Tripp, J. Am. Chem. Soc., 82, 4370 (1960).CrossRefGoogle Scholar
  2. 2.
    V. L. Gein, L. F. Gein, and A. V. Kataeva, Khim. Geterotsikl. Soedin., 1692 (1999). [Chem. Heterocycl. Compd., 35, 1487 (1999)].Google Scholar
  3. 3.
    V. L. Gein, E. V. Voronina, and Yu. S. Andreichikov, Zh. Org. Khim., 27, 1951 (1991).Google Scholar
  4. 4.
    T. A. Silina, N. A. Pulina, L. F. Gein, and V. L. Gein, Khim. Geterotsikl. Soedin., 844 (1998). [Chem. Heterocycl. Compd., 34, 739 (1998)].Google Scholar
  5. 5.
    Yu. S. Andreichikov, S. G. Pitirimova, R. F. Saraeva, V. L. Gein, G. D. Plakhina, and L. A. Voronova, Khim. Geterotsikl. Soedin., 407 (1978). [Chem. Heterocycl. Compd., 14, 336 (1978)].Google Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • V. L. Gein
    • 1
  • M. A. Mar’yasov
    • 1
  • T. A. Silina
    • 1
  1. 1.Perm’ State Pharmaceutical AcademyPermRussia

Personalised recommendations