One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles |
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Authors: | Manning James R Davies Huw M L |
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Affiliation: | Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000, USA. |
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Abstract: | A concise one-pot synthesis of highly functionalized pyridines has been developed. The first step in the reaction sequence is the formal insertion of rhodium vinylcarbenoids across the N-O bond of isoxazoles. Upon heating, the insertion products undergo a rearrangement to give 1,4-dihydropyridines. DDQ oxidation then affords the corresponding pyridines in 31-84% yield. The process has proven general with a range of carbenoid and isoxazole components and represents a unique disconnection strategy for the synthesis of functionalized pyridines. |
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