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An unexpected tetracyclic product isolated during the synthesis of biscoumarins catalyzed by [MIM(CH2)4SO3H][HSO4]: Characterization and X-ray crystal structure of 7-(2-hydroxy-4-oxo-4H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one
Authors:Niloofar Tavakoli-Hoseini  Majid M HeraviFatemeh F Bamoharram  Abolghasem DavoodniaMitra Ghassemzadeh
Institution:
  • a Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
  • b Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran
  • c Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran
  • Abstract:Under solvent-free conditions and in the presence of 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate MIM(CH2)4SO3H]HSO4], a Brønsted acidic ionic liquid, the reaction of aromatic aldehydes with 4-hydroxycoumarin has been investigated. A wide range of aromatic aldehydes easily undergoes condensation with 4-hydroxycoumarin to afford biscoumarins with good purity in excellent yields. However, reaction of 2-hydroxybenzaldehyde with 4-hydroxycoumarin gave, not the corresponding biscoumarin, but a tetracyclic compound, 7-(2-hydroxy-4-oxo-4H-chromen-3-yl)-6H,7H-chromeno4,3-b]chromen-6-one, in high yield.
    Keywords:Biscoumarins  4-Hydroxycoumarin  Ionic liquid  Unexpected product
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