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 |
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Authors: | Niloofar Tavakoli-Hoseini Majid M HeraviFatemeh F Bamoharram Abolghasem DavoodniaMitra Ghassemzadeh |
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Institution: | a Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iranb Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iranc Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran |
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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. |
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Keywords: | Biscoumarins 4-Hydroxycoumarin Ionic liquid Unexpected product |
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