Russian Journal of Organic Chemistry

, Volume 44, Issue 11, pp 1671–1685 | Cite as

Synthesis of nitrogen- and oxygen-containing macrocycles with several polyamine and anthracene or anthraquinone fragments in reactions of palladium-catalyzed amination

  • A. D. Averin
  • E. P. Ranyuk
  • A. K. Buryak
  • I. P. Beletskaya
Article

Abstract

Palladium-catalyzed amination of 1,8-dichloroanthracene and 1,8-dichloroanthraquinone with polyamines made it possible to synthesize bis(haloaryl)-substituted polyamines and oxadiamines, 1,8-bis-(polyamino)substituted anthracenes and anthraquinones. The dependence of the yield of synthesized main and side products on the reaction conditions and on the nature of initial compounds was investigated. The cyclization of compounds obtained was performed leading to cyclodimers and cyclotrimers, and the limitations of this method were established. A possibility was examined of preparation of N,N-diarylated polyamines derivatives in reactions with excess 1,8-dichloroanthracene or 1,8-dichloroanthraquinone.

Keywords

Anthracene Anthraquinone Macrocycle Oily Substance BINAP 

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Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • A. D. Averin
    • 1
  • E. P. Ranyuk
    • 1
  • A. K. Buryak
    • 2
  • I. P. Beletskaya
    • 1
  1. 1.Moscow State UniversityMoscowRussia
  2. 2.Frumkin Institute of Physical Chemistry and ElectrochemistryRussian Academy of SciencesMoscowRussia

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