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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 1, pp 66–69 | Cite as

Synthesis of unsaturated derivatives of 2,5-dimethyl-4-phenylpyridine and 3-methyl-2-azafluorene

  • N. S. Prostakov
  • K. I. Furnaris
  • L. M. Kirillova
  • M. A. Galiullin
  • V. P. Zvolinskii
  • B. Kh. Sisimbina
Article
  • 31 Downloads

Abstract

A substituted butadiene — 1-phenyl-4-(5-methyl-4-phenyl-2-pyridyl)buta-1,3-diene with a trans, trans configuration — was obtained by condensation of 2,5-dimethyl-4-phenylpyridine with cinnamaldehyde. Two 3-methyl-9-cinnamylidene-2-azafluorene isomers are formed as a result of condensation of the same aldehyde with 3-methyl-2-azafluorene. Data from the PMR and IR spectra were used to prove the configuration of the compounds obtained. It was established that the condensation of 3-methyl-2-azafluorene with salicylaldehyde gives 3-methyl-9-(2-hydroxybenzylidene)-2-azafluorene, which has a zwitterionic structure, and 1,2-bis(3-methyl-2-aza-9-fluorenylidene)ethane. Ideas regarding the chemical mechanism of the formation of the latter are presented. The preparation of an unsaturated alcohol — 3-methyl-9-allyl-2-aza-9-fluorenol — is described.

Keywords

Alcohol Organic Chemistry Aldehyde Ethane Diene 
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

  • N. S. Prostakov
    • 1
  • K. I. Furnaris
    • 1
  • L. M. Kirillova
    • 1
  • M. A. Galiullin
    • 1
  • V. P. Zvolinskii
    • 1
  • B. Kh. Sisimbina
    • 1
  1. 1.Practice Lumumba International-Friendship UniversityMoscow

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