Iodocyclization versus diiodination in the reaction of 3-alkynyl-4-methoxycoumarins with iodine: synthesis of 3-iodofuro[2,3-b]chromones |
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Authors: | Raffa Guillaume Belot Sébastien Balme Geneviève Monteiro Nuno |
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Institution: | Université Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS, UMR 5246 du CNRS), CPE Lyon, 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex, France. |
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Abstract: | The reaction of 3-alkynyl-4-methoxycoumarins with molecular iodine in chlorinated solvents allows access to 3-iodofurochromones in good to excellent yields as the result of a iodocyclization-demethylation process. Competitive diiodination of the coumarin acetylene moiety could be eliminated by simply performing the reactions in refluxing 1,2-dichloroethane, owing to the thermal instability of the resulting (E)-1,2-diiodoethenylcoumarins. |
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