Synthesis of isocoumarins and alpha-pyrones via tandem Stille reaction/heterocyclization |
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Authors: | Cherry Khalil Parrain Jean-Luc Thibonnet Jérôme Duchêne Alain Abarbri Mohamed |
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Affiliation: | Laboratoire de Synthèse et Physico-Chimie Organique et Thérapeutique, Faculté des Sciences de Tours, Parc de Grandmont, EA 3857, 37200 Tours, France. |
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Abstract: | A general route to alpha-pyrones and 3-substituted isocoumarins from (Z)-iodovinylic acids 1a-f or 2-iodobenzoic acids 4a-c is described, including compounds bearing a substituent on the aromatic ring. Treatment of (Z)-beta-iodovinylic acids 1a-f or 2-iodobenzoic acids 4a-c with various allenyltributyltin reagents in the presence of palladium acetate, triphenylphosphine, and tetrabutylammonium bromide in dimethylformamide provided good yields of the corresponding alpha-pyrones 3a-k or 3-substituted isocoumarins 5a-g via tandem Stille reaction and 6-endo-dig oxacyclization. |
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