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Chemistry of Heterocyclic Compounds

, Volume 40, Issue 10, pp 1295–1299 | Cite as

Chemistry of acyl(imidoyl)ketenes. 8*. Thermolysis of 3-alkoxycarbonyl- 5-phenyl-1,2,4,5-tetrahydropyrrolo[1,2-a]- quinoxaline-1,2,4-triones. Structure of 2-(3-oxo-4-phenyl-3,4-dihydro-2-quinoxalinyl)- 2,4-di(ethoxycarbonyl)-6-phenyl-2,3,5,6-tetrahydro- 1h-pyrido[1,2-a]quinoxaline-1,3,5-trione

  • A. N. Maslivets
  • Z. G. Aliev
  • O. P. Krasnykh
  • O. V. Golovnina
  • L. O. Atovmyan
Article
  • 39 Downloads

Abstract

3-Alkoxycarbonylmethylene-1-phenyl-1,2,3,4-tetrahydro-2-quinoxalones, obtained by the interaction of dialkyl esters of oxaloacetic acid and N-phenyl-o-phenylenediamine, react with oxalyl chloride with the formation of 3-alkoxycarbonyl-5-phenyl-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxaline-1,2,4-triones. Alkoxycarbonyl(2-oxo-1-phenyl-1,2-dihydro-3-quinoxalinyl)ketenes, generated on thermal decarbonylation of the latter, are stabilized by participation in a [4+2] cyclodimerization reaction with the formation of 2,4-di(alkoxycarbonyl)-2-(3-oxo-4-phenyl-3,4-dihydro-2-quinoxalinyl)-6-phenyl-2,3,5,6-tetrahydro-1H-pyrido[1,2-a]quinoxaline-1,3,5-triones. The crystal and molecular structure of the di(ethoxycarbonyl) derivative have been investigated by X-ray structural analysis.

Keywords

alkoxycarbonyl(imidoyl)ketene acyl(imidoyl)ketene pyrroledione crystal and molecular structure [4 + 2] cyclodimerization 

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Copyright information

© Springer Science+Business Media, Inc. 2004

Authors and Affiliations

  • A. N. Maslivets
    • 1
  • Z. G. Aliev
    • 2
  • O. P. Krasnykh
    • 1
  • O. V. Golovnina
    • 1
  • L. O. Atovmyan
    • 2
  1. 1.Perm State UniversityPermRussia
  2. 2.Institute of the Problems of Chemical PhysicsRussian Academy of SciencesChernogolovka, Moscow regionRussia

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