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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 7, pp 1129–1131 | Cite as

Reaction of 2-pyridylselenenyl bromide with divinyl selenide

  • V. A. Potapov
  • D. A. Malinovich
  • S. V. AmosovaEmail author
  • Yu. Yu. Rusakov
  • K. K. Bhasin
Article

The pyridine ring is an important pharmaceutical scaffold, and pyridine derivatives exhibit various biological activities [1]. Many alkaloids with annelated structures contain the pyridine ring [1].

In this paper, we elaborate on novel approaches to annelation of chalcogen-containing rings [2, 3, 4, 5, 6]. One of the important intermediates that can serve for the annelation of chalcogen-containing rings to the pyridine cycle is 2-pyridylselenenyl halides [7, 8]. Although 2-pyridylselenenyl chloride was used in annelation reactions [7, 8], 2-pyridylselenenyl bromide was not. It was reported that 2-pyridineselenenyl bromide reacted with styrene in methanol to give the solvoadduct – 1-methoxy-1-phenyl-2-(2-pyridylselanyl)ethane – in quantitative yield [9]. Annelation products were not formed in this reaction.

We found that the reaction of 2-pyridylselenenyl bromide ( 1) with divinyl selenide [ 10, 11] led to a previously unknown annelated heterocycle, 3-(vinylselanyl)-2,3-dihydro[1,...

Keywords

divinyl selenide pyridineselenenyl bromide electrophilic addition nucleophilic substitution 

Notes

Financial support of the Russian Foundation for Basic Research (grants Nos. 10-03-00543 and 10-03-92666) is gratefully acknowledged.

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Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • V. A. Potapov
    • 1
  • D. A. Malinovich
    • 1
  • S. V. Amosova
    • 1
    Email author
  • Yu. Yu. Rusakov
    • 1
  • K. K. Bhasin
    • 2
  1. 1.A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of SciencesIrkutskRussia
  2. 2.Department of Chemistry and Centre of Advanced Studies in ChemistryPanjab UniversityChandigarhIndia

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