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 language | English |
|---|---|
| Pages (from-to) | 2787-2797 |
| Number of pages | 11 |
| Journal | Tetrahedron |
| Volume | 63 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 2007 Mar 26 |
Keywords
- Cycloaddition
- Functionalized 3,4-pyridyne
- Functionalized organomagnesium reagents
- Halogen-magnesium exchange
- Magnesium
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Lin, W., Chen, L., & Knochel, P. (2007). Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates. Tetrahedron, 63(13), 2787-2797. https://doi.org/10.1016/j.tet.2007.01.027