Molecular Diversity

, Volume 15, Issue 2, pp 445–450 | Cite as

A mild and efficient method for the synthesis of a new class of furo[3,2-c]chromenes in aqueous media

  • Mohammad A. Khalilzadeh
  • Zinatossadat Hossaini
  • Faramarz Rostami Charati
  • Sara Hallajian
  • Mehdi Rajabi
Full-Length Paper


An efficient synthesis of 2-hydroxy-3-[2-oxo-2-phenylethylidene]-2-phenyl-2, 3-dihydro-4 H-furo[3, 2-c]chromene-4(2H)-one is described. This involves the reaction between dibenzoylacetylene and 4-hydroxycoumarine in the presence of NaH (10 mol %) in nearly quantitative yield. Treatment of this heterocyclic system with trimethyl chlorosilane in CHCl3 leads quantitatively to 4-oxo-3-[2-oxo-2-phenylethylidene]-2-phenyl-3H, 4H-furo[3,2-c]chromene-1-ium chloride. Direct addition of nucleophiles, such as alcohols, amines or trialkyl phosphites to this salt in water as the solvent produces functionalized 2-phenyl-4H-furo[3,2-c] chromen derivatives in excellent yields.


Oxonium cation Furo[3,2-c]chromene-1-ium cation Naphthofurans 4-Hydroxycoumarine Dibenzoylacetylene Chromenes 


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Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  • Mohammad A. Khalilzadeh
    • 1
  • Zinatossadat Hossaini
    • 1
  • Faramarz Rostami Charati
    • 2
  • Sara Hallajian
    • 1
  • Mehdi Rajabi
    • 3
  1. 1.Chemistry DepartmentIslamic Azad UniversityMazandaranIran
  2. 2.Faculty of ScienceGonbad Higher Education CenterGonbadIran
  3. 3.Department of Medicine, Surgery and Dentistry and Centre of Molecular and Cellular Imaging (IMAGO)Università degli Studi di MilanoMilanItaly

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