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

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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

Content Provider	Semantic Scholar
Author	Qareaghaj, Omid Hosseinchi Mashkouri, Sara Naimi-Jamal, Mohammad Reza Kaupp, Gerd
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	PDF HTM / HTML
DOI	10.1039/C4RA06603K
Volume Number	4
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2014/ra/c4ra06603k
Alternate Webpage(s)	http://www.rsc.org/suppdata/ra/c4/c4ra06603k/c4ra06603k1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/C4RA06603K
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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