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

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Abstract

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.

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Authors and Affiliations

  1. Chemistry Department, Islamic Azad University, Qaemshahr Branch, P.O. Box 163, Mazandaran, Iran

    Mohammad A. Khalilzadeh, Zinatossadat Hossaini & Sara Hallajian

  2. Faculty of Science, Gonbad Higher Education Center, PO Box 163, Gonbad, Iran

    Faramarz Rostami Charati

  3. Department of Medicine, Surgery and Dentistry and Centre of Molecular and Cellular Imaging (IMAGO), Università degli Studi di Milano, Milan, Italy

    Mehdi Rajabi

Authors
  1. Mohammad A. Khalilzadeh
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  2. Zinatossadat Hossaini
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  3. Faramarz Rostami Charati
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  4. Sara Hallajian
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  5. Mehdi Rajabi
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Correspondence to Mohammad A. Khalilzadeh.

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Khalilzadeh, M.A., Hossaini, Z., Charati, F.R. et al. A mild and efficient method for the synthesis of a new class of furo[3,2-c]chromenes in aqueous media. Mol Divers 15, 445–450 (2011). https://doi.org/10.1007/s11030-010-9264-3

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  • DOI: https://doi.org/10.1007/s11030-010-9264-3

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