1. Library-directed Solution- and Solid-phase Synthesis of 2,4-Disubstituted Pyridines: One-pot Approach through 6 π-Azaelectrocyclization
- Author
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Hiroshi Tsuchikawa, Sho Hatano, Toyoharu Kobayashi, Shigeo Katsumura, Taku Sakaguchi, Koichi Fukase, and Katsunori Tanaka
- Subjects
chemistry.chemical_classification ,Spectrometry, Mass, Electrospray Ionization ,Pyridines ,Organic Chemistry ,Spectrometry, X-Ray Emission ,Stereoisomerism ,Sequence (biology) ,General Chemistry ,Silanes ,Biochemistry ,Catalysis ,Sulfonamide ,Solutions ,Chromatographic separation ,chemistry.chemical_compound ,Solid-phase synthesis ,chemistry ,Cyclization ,Pyridine ,Vinyl iodide ,Combinatorial Chemistry Techniques ,Organic chemistry ,Palladium catalyst ,Linker ,Palladium - Abstract
An efficient one-pot synthetic procedure for the synthesis of 2,4-disubstituted pyridines has been successfully established. The method proceeds through a 6pi-azaelectrocyclization-aromatization sequence. Using this method, a wide variety of pyridine structures substituted at the 2-position have been rapidly constructed from vinyl stannanes, vinyl iodide, sulfonamide, and a palladium catalyst. The method was further applied to the solid-phase synthesis wherein the use of a "traceless" sulfonamide linker enabled the rapid preparation of a small library of pyridines with high purity, without any chromatographic separation.
- Published
- 2009