Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Efficient One-Step Synthesis of 2-Arylfurans by Ceric Ammonium Nitrate (CAN)-Mediated Cycloaddition of 1,3-Dicarbonyl Compounds to Alkynes

  • Published : 1998.10.20
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Abstract

An efficient method for construction of 2-arylfiirans has been developed by ceric(IV) ammonium nitratemediated oxidative cycloaddition of cyclic and acyclic 1,3-dicarbonyl compounds to several alkynes. Reactions of 1,3-cyclohexanedione, 1,3-cyclopentanedione, and 2,4-pentanedione with several alkynes furnish 2-arylfurans in 26-75% yields. Extension of this technology to more complex 4-hydroxy-2-quinolone and 3-hydroxy-lH-phenalen-l-one with phenylacetylene also affords furoquinolinone and ftirophenalenone derivative in moderate yields. Reaction of 4-hydroxycoumarins with phenylacetylene give linear and angular furocoumarin derivatives as a mixture of regioisomer in good yields. The mechanistic pathway for the formation of 2-arylfurans has been also described.

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