Library-directed solution- and solid-phase synthesis of 2,4-disubstituted pyridines: one-pot approach through 6pi-azaelectrocyclization.
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.
Sakaguchi
Taku
T
Department of Chemistry and Open Research Center on Organic Tool Molecules, School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo 669-1337, Japan.
Kobayashi
Toyoharu
T
Hatano
Sho
S
Tsuchikawa
Hiroshi
H
Fukase
Koichi
K
Tanaka
Katsunori
K
Katsumura
Shigeo
S
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry; D012996:Solutions / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013052:Spectrometry, X-Ray Emission / Q000379:methods; D013237:Stereoisomerism
D011725:Pyridines; D012821:Silanes; D012996:Solutions; D010165:Palladium