NDLI: 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

Content Provider	Royal Society of Chemistry (RSC)
Author	Kaupp, Gerd Mashkouri, Sara Naimi-Jamal, M. Reza Qareaghaj, Omid Hosseinchi
Copyright Year	2014
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.
Starting Page	48191
Ending Page	48201
Page Count	11
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	4
Issue Number	89
Journal	RSC Advances
DOI	10.1039/c4ra06603k
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Stoichiometry Dimedone Malononitrile Nuclear magnetic resonance spectroscopy 1,3-Cyclohexanedione Solvent Resorcinol
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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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