Library‐directed Solution‐ and Solid‐phase Synthesis of 2,4‐Disubstituted Pyridines: One‐pot Approach through 6 π‐Azaelectrocyclization |
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| Authors: | Taku Sakaguchi Toyoharu Kobayashi Dr Sho Hatano Hiroshi Tsuchikawa Dr Koichi Fukase Prof?Dr Katsunori Tanaka Dr Shigeo Katsumura Prof?Dr |
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| Institution: | 1. 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), Fax: (+81)?79‐565‐9077;2. Department of Chemistry, Graduate School of Science, Osaka University, 1‐1 Machikaneyama, Toyonaka, Osaka 560‐0043 (Japan) |
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| Abstract: | An efficient one‐pot synthetic procedure for the synthesis of 2,4‐disubstituted pyridines has been successfully established. The method proceeds through a 6π‐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. |
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| Keywords: | cross‐coupling electrocyclic reactions nitrogen heterocycles solid‐phase synthesis sulfonamides |
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