Sívek Roman, Bures Filip, Pytela Oldrich, Kulhánek Jirí
Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, nám. Cs. legií 565, Pardubice, CZ-532 10, Czech Republic.
Molecules. 2008 Sep 25;13(9):2326-39. doi: 10.3390/molecules13092326.
Twelve new imidazole-based potential bi- and tridentate ligands were synthesized and characterized. Whereas in the first series the alpha-amino acid and imidazole moieties were linked by an amino bond, in the second series the tridentate ligands, containing two imidazole groups, were separated by an amide bond. The first series was obtained by the reductive amination of 2-phenylimidazole-4-carboxaldehyde with alpha-amino acid esters. The tridentate ligands were prepared from 2-phenylimidazole-4-carboxylic acid and chiral amines. In the Henry reaction, the amines were revealed as a more reactive species than the less nucleophilic amides, however the enantiomeric excesses were generally poor.
合成并表征了12种新型基于咪唑的潜在双齿和三齿配体。在第一个系列中，α-氨基酸和咪唑部分通过氨基键连接，而在第二个系列中，含有两个咪唑基团的三齿配体通过酰胺键隔开。第一个系列是通过2-苯基咪唑-4-甲醛与α-氨基酸酯的还原胺化反应得到的。三齿配体由2-苯基咪唑-4-羧酸和手性胺制备。在亨利反应中，胺被证明是比亲核性较弱的酰胺更具反应活性的物种，然而对映体过量通常较差。
