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Chemistry of Heterocyclic Compounds

, Volume 45, Issue 2, pp 176–181 | Cite as

Reaction of 2-pyridyllithium with azine N-oxides. Simple and convenient method for the synthesis of 2,2′-bipyridine 1-oxide and 2,2′:6′,2″:6″2′″-tetrapyridine 1′-oxide

  • I. S. Kovalev
  • V. L. Rusinov
  • O. N. ChupakhinEmail author
Article

In the reaction of 2-pyridyllithium with quinoline 1-oxide and isoquinoline 2-oxide a nucleophilic substitution of hydrogen occurs to form the corresponding pyridin-2-ylquinolines. A dimerization of the substrate occurs with pyridine 1-oxide, 2,2′-bipyridine 1-oxide or quinoxaline N-oxide. A similar dimerization in good yield occurs when treating azine N-oxides with tert-butyllithium and this serves as a simple and convenient method for preparing bi- and tetrapyridines.

Keywords

azine N-oxides ligands oligopyridines dimerization nucleophilic substitution of hydrogen 

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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • I. S. Kovalev
    • 1
  • V. L. Rusinov
    • 1
  • O. N. Chupakhin
    • 1
    • 2
    Email author
  1. 1.Ural State Technical University – UPIYekaterinburgRussia
  2. 2.I. Ya. Postovsky Institute of Organic ChemistryUral Branch of the Russian Academy of SciencesYekaterinburgRussia

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