Et3N-induced demethylation-annulation of 3-alkynyl-4-methoxy-2-pyridones and structurally related compounds in the synthesis of furan-fused heterocycles |
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Authors: | Conreaux David Belot Sébastien Desbordes Philippe Monteiro Nuno Balme Geneviève |
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Institution: | ICBMS, Institut de Chimie et Biochimie Moléculaire et Supramoléculaire, CNRS UMR 5246, Université Lyon 1, ESCPE Lyon. 43, Bd du 11 Novembre 1918, 69622 Villeurbanne, France. |
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Abstract: | Various 3-iodo-4-methoxypyridin-2-ones and related pyrone and coumarin derivatives have been demonstrated as readily available precursors of 2-substituted furan-fused heterocycles by means of in situ sequential Sonogashira-acetylide coupling, dealkylation, and regioselective furan annulation reactions. A Et3N-induced S(N)2 process has been established that accounts for the dealkylation process. |
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