Pyridine-oriented transannular C-H functionalization of arenes
Yanchun Hou1, Jianwei Liu1, Yi Tian1
1School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng Street, Chongqing, 400044, China. libs@cqu.edu.cn.
A novel pyridine-oriented Friedel-Crafts alkylation reaction creates fused seven- or eight-membered rings. These structures are valuable precursors for pharmaceuticals and other complex molecules.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Friedel-Crafts alkylation is a fundamental carbon-carbon bond-forming reaction.
- Transannular reactions offer unique pathways to complex ring systems.
- Pyridine-containing heterocycles are prevalent in pharmaceuticals.
Purpose of the Study:
- To develop a novel pyridine-oriented transannular Friedel-Crafts alkylation.
- To synthesize pyridine-containing fused seven- and eight-membered rings.
- To explore the synthetic utility of these novel ring systems.
Main Methods:
- Employing a pyridine-oriented transannular Friedel-Crafts alkylation.
- Investigating thermodynamically unfavorable reaction conditions.
- Characterizing the resulting fused heterocyclic products.
Main Results:
- Successfully synthesized a series of pyridine-containing fused seven- and eight-membered rings.
- Demonstrated the feasibility of the transannular Friedel-Crafts alkylation despite unfavorable thermodynamics.
- Obtained products with skeletons similar to marketed pharmaceuticals.
Conclusions:
- The developed pyridine-oriented transannular Friedel-Crafts alkylation is a viable synthetic route.
- The synthesized fused ring systems serve as valuable intermediates for pharmaceutical development.
- These compounds can be further transformed into synthetically useful pleiadienes.
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