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Issue 89, 2014
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Ball milling for the quantitative and specific solvent-free Knoevenagel condensation + Michael addition cascade in the synthesis of various 2-amino-4-aryl-3-cyano-4H-chromenes without heating

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Abstract

Ball milling is used as a facile, efficient, cheap, and environmentally friendly procedure for the solvent-free three-component reaction of aromatic aldehydes with malononitrile and dimedone, or 1,3-cyclohexanedione, resorcinol, and α- and β-naphthol. The reactions proceed quantitatively at room temperature by milling stoichiometric mixtures of the reagents in the presence of 10 mol% Na2CO3. This method offers the advantages of short reaction times, low cost, quantitative yields and simple work-up with no need of any organic solvent. It is thus enviro-economic without producing dangerous wastes. The orientation selectivity with β-naphthol and resorcinol is discussed. Existing structural misattributions are pointed out and clarified by 1H NMR spin coupling analysis.

Graphical abstract: Ball milling for the quantitative and specific solvent-free Knoevenagel condensation + Michael addition cascade in the synthesis of various 2-amino-4-aryl-3-cyano-4H-chromenes without heating

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Publication details

The article was received on 03 Jul 2014, accepted on 02 Sep 2014 and first published on 11 Sep 2014


Article type: Paper
DOI: 10.1039/C4RA06603K
Citation: RSC Adv., 2014,4, 48191-48201
  • Open access: Creative Commons BY-NC license
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    Ball milling for the quantitative and specific solvent-free Knoevenagel condensation + Michael addition cascade in the synthesis of various 2-amino-4-aryl-3-cyano-4H-chromenes without heating

    O. H. Qareaghaj, S. Mashkouri, M. R. Naimi-Jamal and G. Kaupp, RSC Adv., 2014, 4, 48191
    DOI: 10.1039/C4RA06603K

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