Boukis Andreas C, Monney Baptiste, Meier Michael A R
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Materialwissenschaftliches Zentrum MZE, Building 30.48, Straße am Forum 7, 76131 Karlsruhe, Germany.
Beilstein J Org Chem. 2017 Jan 9;13:54-62. doi: 10.3762/bjoc.13.7. eCollection 2017.
The Biginelli reaction was combined with the Passerini reaction for the first time in a sequential multicomponent tandem reaction approach. After evaluation of all possible linker components and a suitable solvent system, highly functionalized dihydropyrimidone-α-acyloxycarboxamide compounds were obtained in good to excellent yields. In a first reaction step, different 3,4-dihydropyrimidin-2(1)-one acids were synthesized, isolated and fully characterized. These products were subsequently used in a Passerini reaction utilizing a dichloromethane/dimethyl sulfoxide solvent mixture. By variation of the components in both multicomponent reactions, a large number of structurally diverse compounds could be synthesized. In addition, a one-pot Biginelli-Passerini tandem reaction was demonstrated. All products were carefully characterized via 1D and 2D NMR as well as IR and HRMS.
首次采用连续多组分串联反应方法将Biginelli反应与Passerini反应相结合。在评估了所有可能的连接体成分和合适的溶剂体系后，以良好至优异的产率获得了高度官能化的二氢嘧啶酮-α-酰氧基羧酰胺化合物。在第一步反应中，合成、分离并充分表征了不同的3,4-二氢嘧啶-2(1)-酮酸。随后，这些产物用于使用二氯甲烷/二甲基亚砜溶剂混合物的Passerini反应。通过改变两个多组分反应中的成分，可以合成大量结构多样的化合物。此外，还展示了一锅法Biginelli-Passerini串联反应。所有产物均通过一维和二维核磁共振以及红外光谱和高分辨质谱进行了仔细表征。
