Chemistry of Heterocyclic Compounds

, Volume 14, Issue 5, pp 534–538 | Cite as

Reaction of substituted 2-vinylpyridines with azo dienophiles

  • P. B. Terent'ev
  • N. G. Kotova
  • A. N. Kost


The reaction of 2-(1-alkoxyvinyl)pyridines with dimethyl azodicarboxylate proceeds primarily via a scheme involving addition to the vinyl substituent to give a mixture of cis- and trans-2-[1-alkoxy-2-(N, N'-dicarbomethoxyhydrazino)-vinyl] pyridines, which undergo partial reaction with a second molecule of azodicarboxylic acid ester via a 1, 4-cycloaddition scheme to give substituted 1, 2, 3, 4-tetrahydro-5-azacinnolines. 2-(1-Bromovinyl)pyridine does not react with dimethyl azodicarboxylate. 1-Phenyl-1, 3, 4-triazoline-2, 5-dione reacts with 2-(1-alkoxyvinyl)pyridines also via a scheme involving addition to the vinyl substituent, and its reaction with 2-(1-bromovinyl)pyridine gives 1, 2-bis (carbomethoxy)-1, 2-dihydro-5-azacinnoline.


Ester Organic Chemistry Pyridine Dimethyl Vinyl 
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Literature cited

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Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • P. B. Terent'ev
    • 1
  • N. G. Kotova
    • 1
  • A. N. Kost
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscow

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