A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization |
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Authors: | Aillaud Isabelle Bossharth Emmanuel Conreaux David Desbordes Philippe Monteiro Nuno Balme Geneviève |
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Institution: | Laboratoire de Synthèse Organométallique et Molécules Bioactives, CNRS UMR 5181, Université Claude Bernard-Lyon I, ESCPE Lyon. 43, Bd du 11 Novembre 1918, 69622 Villeurbanne, France. |
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Abstract: | reaction: see text] N-Methyl-4-alkoxy-3-alkynylpyridin-2(1H)-ones readily undergo iodine-promoted 5-endo-heteroannulation under mild conditions to 3-iodofuropyridinium triiodide salts in moderate to good yields. The latter may be dealkylated in situ upon exposure to an iodide anion to provide the corresponding 3-iodofuro2,3-b]pyridin-4(1H)-ones. The same strategy applies to the formation of furo2,3-b]quinolin-4(9H)-ones. |
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