title: Library-directed solution- and solid-phase synthesis of 2,4-disubstituted pyridines: one-pot approach through 6pi-azaelectrocyclization.
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.
authors.affiliation: 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.
authors.forename: Taku
authors.initials: T
authors.lastname: Sakaguchi
authors.forename: Toyoharu
authors.initials: T
authors.lastname: Kobayashi
authors.forename: Sho
authors.initials: S
authors.lastname: Hatano
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tsuchikawa
authors.forename: Koichi
authors.initials: K
authors.lastname: Fukase
authors.forename: Katsunori
authors.initials: K
authors.lastname: Tanaka
authors.forename: Shigeo
authors.initials: S
authors.lastname: Katsumura
mesh_terms: 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
chemical_list: D011725:Pyridines; D012821:Silanes; D012996:Solutions; D010165:Palladium