Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates

Wen-Wei Lin, Ling Chen, Paul Knochel

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The preparation of functionalized 3,4-pyridynes of type 1 as highly reactive intermediates has been achieved by the controlled elimination of readily generated 2-magnesiated diaryl sulfonates of type 2 obtained by a low temperature I/Mg- or Br/Mg-exchange starting from the corresponding halides of type 3. After trapping with furan, moderate to good yields of the desired functionalized cycloadducts of type 4 are obtained. The addition of a magnesium arylthiolate or magnesium phenylselenide to 3,4-pyridyne followed by quenching with an electrophile is also described.

Original languageEnglish
Pages (from-to)2787-2797
Number of pages11
JournalTetrahedron
Volume63
Issue number13
DOIs
Publication statusPublished - 2007 Mar 26

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Magnesium
Quenching
Temperature
furan

Keywords

  • Cycloaddition
  • Functionalized 3,4-pyridyne
  • Functionalized organomagnesium reagents
  • Halogen-magnesium exchange
  • Magnesium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates. / Lin, Wen-Wei; Chen, Ling; Knochel, Paul.

In: Tetrahedron, Vol. 63, No. 13, 26.03.2007, p. 2787-2797.

Research output: Contribution to journalArticle

Lin, Wen-Wei ; Chen, Ling ; Knochel, Paul. / Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates. In: Tetrahedron. 2007 ; Vol. 63, No. 13. pp. 2787-2797.
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