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

Authors

  • И. С. Ковалев Ural State Technical University – UPI, Yekaterinburg 620002
  • В. Л. Русинов Ural State Technical University – UPI, Yekaterinburg 620002
  • О. Н. Чупахин Ural State Technical University – UPI, Yekaterinburg 620002 I. Ya. Postovsky Institute of Organic Chemistry, Ural Branch of the Russian Academy of Sciences, Yekaterinburg 620219

DOI:

https://doi.org/10.1007/6819

Keywords:

azine N-oxides, ligands, oligopyridines, dimerization, nucleophilic substitution of hydrogen

Abstract

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.

Kovalev, I. S.; Rusinov, V. L.; Chupakhin, O. N.  Chem. Heterocycl. Compd. 2009, 45, 176. [Khim. Geterotsikl. Soedin. 2009, 223.]

For this article in the English edition see DOI 10.1007/s10593-009-0247-1


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Published

2022-05-23

Issue

No. 2 (2009)

Section

Original Papers