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Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties
ACS Combinatorial Science ( IF 3.903 ) Pub Date : 2018-09-24 00:00:00 , DOI: 10.1021/acscombsci.8b00137
Damiano Rocchi 1 , Juan F. González 1 , Jorge Gómez-Carpintero 1 , Víctor González-Ruiz 2 , M. Antonia Martín 2 , Vellaisamy Sridharan 3, 4 , J. Carlos Menéndez 1
Affiliation  

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.

中文翻译:

库三组分合成与嵌入式β氨基酯基团-三联苯衍生物

烷基-或芳基胺之间的三组分反应,β酮酯和查耳酮在回流的含Ce(IV)铵的催化量的乙醇允许高度取代的二氢的大型文库的构建含β -烷基氨基-三联苯衍生物-或β-芳基氨基酯部分。该过程产生三个新的键和一个环,并以高原子经济性进行,只有两个分子的水是唯一的副产物。另一个多米诺骨牌工艺(其中原始的MCR用随后的aza Michael / retro-aza Michael序列进行伸缩)允许一锅制备带有N的化合物库-未取代的β-氨基酯片段。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基醌存在下我们化合物中心环的芳构化。该反应序列不影响属于氨基组分的立体异构中心的完整性。
更新日期:2018-09-24
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