Chemistry of Heterocyclic Compounds

, Volume 9, Issue 1, pp 55–59 | Cite as

Properties of a multiple bond conjugated with the pyridine ring

X. Change in the orientation of the addition of diazomethane to the polarized multiple bond of substituted vinylpyridines
  • P. B. Terent'ev
  • S. M. Vinogradova
  • A. N. Kost
  • A. G. Strukovskii


The products of the addition of diazomethane to the double bond of α-, β-, and γ-vinyl-pyridines, 2-propenyl-, 2-styryl-, and 2-(p-nitrostyryl)pyridines, and β-(2-pyridyl)acrylic acid were obtained. When a hydrogen atom or alkyl or phenyl group is present in the β-position of the vinyl group, 3-pyridyl-Δ2-pyrazolines are formed (they are isolated as the acetyl derivatives). Electron-acceptor substituents (COOCH3 and C6H4NO2) in this position disrupt the polarization, and this leads to the formation of a mixture of two isomeric pyrazolines. The primary formation of Δ1-pyrazolines was proved by means of IR and UV spectroscopy.


Phenyl Pyridine Hydrogen Atom Double Bond Vinyl 
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Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1975

Authors and Affiliations

  • P. B. Terent'ev
    • 1
  • S. M. Vinogradova
    • 1
  • A. N. Kost
    • 1
  • A. G. Strukovskii
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityUSSR

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