New tandem reductive rearrangement of 3-furylphthalides into 3-(3-oxoalkyl)isocoumarins

• Published in: Tetrahedron letters Vol. 57; no. 13; pp. 1483 - 1485
• Main Authors: Shpuntov, Pavel M., Shcherbinin, Vitaly A., Abaev, Vladimir T., Butin, Alexander V.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.03.2016; Elsevier
• Subjects: 3-(2-Furyl)phthalide; 3-(3-Oxoalkyl)isocoumarin; Chemistry; Chemistry, Organic; Iodine; Phosphorus; Physical Sciences; Reagents; Rearrangement; Red phosphorus; Science & Technology; Substrates; Synthesis; Tetrahedrons; Transformations; 3-(2-Furyl)phthalide; 3-(3-Oxoalkyl)isocoumarin; Red phosphorus; Rearrangement; Iodine; RECYCLIZATION REACTION; ISOCOUMARINS; DERIVATIVES; RING-CLOSURE
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2016.02.072

[Display omitted] •3-(2-Furyl)phthalides undergo reductive rearrangement under the action of I2/red P.•One-pot procedure for the synthesis of 3-(3-oxoalkyl)isocoumarins was developed.•3-(3-Oxoalkyl)isocoumarins are precursors to antifungal 3-butylisocoumarines. A new tandem transformation of 3-furylphthalides into 3-(3-oxoalkyl)isocoumarins mediated by a red phosphorus/iodine reagent system has been developed. This allows the straightforward preparation of functionalized isocoumarins in good yields using readily available substrates and reagents. The obtained products can be employed in the synthesis of natural 3-butylisocoumarins with antifungal properties.