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Chemistry of Heterocyclic Compounds

, Volume 15, Issue 5, pp 518–526 | Cite as

Cycloaddition of azodicarboxylic acid esters to vinylpyridines

  • P. B. Terent'ev
  • V. G. Kartsev
  • I. K. Yakushenko
  • L. N. Prostakova
  • A. N. Kost
  • I. P. Gloriozov
Article
  • 31 Downloads

Abstract

The reaction of methyl or ethyl esters of azodicarboxylic acid with 3-, 4-, 5-, or 6-alkyl-2-vinylpyridines proceeds via the scheme of the diene synthesis with the participation of the pseuodcarbodiene system of vinylpyridines and leads to the formation of 1,2,3,4-tetrahydro-5-azacinnoline derivatives. In addition to these “monoadducts,” 4-[N,N′-bis(methoxycarbonyl)hydrazino] derivatives are formed in large amounts., The structures of all of the reaction products were proved by the IR, UV, PMR, and mass spectra. The possibility of the application of the computational methods of MO perturbation theory for the prediction of the probability of the formation of various regioisomers is demonstrated.

Keywords

Methyl Ester Ethyl Mass Spectrum Organic Chemistry 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • P. B. Terent'ev
    • 1
  • V. G. Kartsev
    • 1
  • I. K. Yakushenko
    • 1
  • L. N. Prostakova
    • 1
  • A. N. Kost
    • 1
  • I. P. Gloriozov
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscow

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