Unidad de Química Orgánica y Farmacéutica, Departamento de Química en Ciencias Farmacéuticas, Facultad de Farmacia , Universidad Complutense , 28040 Madrid , Spain.
Unidad de Química Analítica, Departamento de Química en Ciencias Farmacéuticas, Facultad de Farmacia , Universidad Complutense , 28040 Madrid , Spain.
ACS Comb Sci. 2018 Dec 10;20(12):722-731. doi: 10.1021/acscombsci.8b00137. Epub 2018 Oct 8.
The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro- m-terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.
在回流的乙醇中，使用催化量的硝酸铈铵，使烷基胺、β-二酮酯和查耳酮发生三组分反应，可以构建一个包含β-烷基氨基-或β-芳氨基酯部分的高度取代的二氢- m-三联苯衍生物的大型文库。该过程生成三个新键和一个环，具有高原子经济性，仅生成两个水分子作为唯一的副产物。另一个多米诺反应，将原始的 MCR 与随后的氮杂迈克尔/反氮杂迈克尔序列缩合，允许一锅法制备具有未取代的 N-β-氨基酯片段的化合物文库。最后，为了扩展这些文库的结构多样性，我们还研究了在二氯二氰醌存在下我们化合物中环的芳构化。该反应序列不影响属于氨基部分的手性中心的完整性。
