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 |
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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 journal › Article
}
TY - JOUR
T1 - Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates
AU - Lin, Wen-Wei
AU - Chen, Ling
AU - Knochel, Paul
PY - 2007/3/26
Y1 - 2007/3/26
N2 - 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.
AB - 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.
KW - Cycloaddition
KW - Functionalized 3,4-pyridyne
KW - Functionalized organomagnesium reagents
KW - Halogen-magnesium exchange
KW - Magnesium
UR - http://www.scopus.com/inward/record.url?scp=33847036007&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33847036007&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.01.027
DO - 10.1016/j.tet.2007.01.027
M3 - Article
AN - SCOPUS:33847036007
VL - 63
SP - 2787
EP - 2797
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 13
ER -