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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 1, pp 114–116 | Cite as

Oxidative amination and hydroxylation of 1,3,7-triazapyrenes in aqueous medium

  • O. P. Demidov
  • I. V. BorovlevEmail author
  • N. A. Saigakova
  • O. A. Nemykina
  • N. V. Demidova
  • S. V. Pisarenko
Article

We have already reported the unusual capacity of 1,3,7-triazapyrenes 1a and 1b [1] and 7-alkyl-1,3,7-triazapyrenium salts [2, 3, 4, 5] to react readily in aqueous solution with O-nucleophilic reagents to give mono- and disubstitution products. This is the result clearly not only of the π-electron deficiency of these compounds but also the specific peri-fusion structure of this heterocyclic system.

The oxidative amination of the most electrophilic heterocycles such as naphthyridines [6] or 1,2,4-tria-zine [7] is carried out by action of a solution of KMnO4 in liquid ammonia. We have discovered, however, that 1,3,7-triazapyrenes 1a and 1b may be aminated in a solution of ammonia in aqueous dioxane in the presence of K3[Fe(CN)6]. The reaction proceeds at 50-55 °C to give 6-amino-1,3,7-triazapyrene (2a) in 95% yield and 6-amino-2-methyl-1,3,7-triazapyrene (2b) in 89% yield.

Keywords

1,3,7-triazapyrenes nucleophilic replacement of hydrogen oxidative amination oxidative hydroxylation 

References

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • O. P. Demidov
    • 1
  • I. V. Borovlev
    • 1
    Email author
  • N. A. Saigakova
    • 1
  • O. A. Nemykina
    • 1
  • N. V. Demidova
    • 1
  • S. V. Pisarenko
    • 1
  1. 1.Stavropol State UniversityStavropolRussia

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