Chemistry of Heterocyclic Compounds

, Volume 27, Issue 7, pp 788–794 | Cite as

Reactions of derivatives of 4a,9-diaza-1,2,4a,9a-tetrahydro-6H-fluorene with nucleophilic reagents and bromine

  • O. Yu. Slabko
  • O. I. Britsina
  • V. A. Kaminskii
Article

Abstract

The reaction of quinone mono- and diimines of the 4a,9-diaza-12,4a,9a-tetrahydro-6H-fluorene series with aniline and thiophenol gives the corresponding 7-monosubstituted derivatives; with o-phenylenediamine and o-aminophenol the corresponding 6,7-annellated products are formed. Methylenequinone imines of this series, and also the 7,8-benzannellated analogs ofdiazahydrofluorenes, do not react with these nucleophiles. The bromination of diazahydrofluorene derivatives involves both the quinoid system and the enamine fragment.

Keywords

Organic Chemistry Aniline Quinone Bromine Enamine 

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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • O. Yu. Slabko
    • 1
  • O. I. Britsina
    • 1
  • V. A. Kaminskii
    • 1
  1. 1.Vladivostok State UniversityVladivostok

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