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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
Article
  • 27 Downloads

Abstract

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.

Keywords

Ester Organic Chemistry Pyridine Dimethyl Vinyl 
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 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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