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

被引：61
作者：
Qareaghaj, Omid Hosseinchi [1 ]
Mashkouri, Sara [1 ]
Naimi-Jamal, M. Reza [1 ]
Kaupp, Gerd [2 ]
机构：
[1] Iran Univ Sci & Technol, Dept Chem, Res Lab Green Organ Synth & Polymers, Tehran 16846, Iran
[2] Carl von Ossietzky Univ Oldenburg, Dept Chem, D-26188 Edewecht, Germany
来源：
RSC ADVANCES | 2014年 / 4卷 / 89期
关键词：
ONE-POT SYNTHESIS; HETEROGENEOUS BASE CATALYST; AQUEOUS-MEDIA; 3-COMPONENT SYNTHESIS; VERSATILE CATALYST; EFFICIENT CATALYST; SOLID-STATE; WASTE-FREE; PHENYLBORONIC ACID; ROOM-TEMPERATURE;
D O I：
10.1039/c4ra06603k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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 alpha- and beta- 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 beta-naphthol and resorcinol is discussed. Existing structural misattributions are pointed out and clarified by H-1 NMR spin coupling analysis.
引用
收藏
页码：48191 / 48201
页数：11
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