Unidad de Química Orgánica y Farmacéutica, Departamento de Química en Ciencias Farmacéuticas, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
Molecules. 2021 Mar 2;26(5):1330. doi: 10.3390/molecules26051330.
The aza-vinylogous Povarov reaction between aromatic amines, α-ketoaldehydes or α-formylesters and α,β-unsaturated dimethylhydrazones was carried out in a sequential three-component fashion under mechanochemical conditions. Following extensive optimization work, the reaction was performed on a vibratory ball mill operating at 20 Hz and using zirconium oxide balls and milling jar, and afforded 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro- 1,5-naphthyridines functionalized at C-2, C-4 and also at C-6, in the latter case. This protocol generally afforded the target compounds in good to excellent yields and diastereoselectivities. A comparison of representative examples with the results obtained under conventional conditions revealed that the mechanochemical protocol affords faster Povarov reactions in comparable yields using a solvent-less environment.
在机械化学条件下，通过芳胺、α-酮醛或α-甲酯和α,β-不饱和二甲基腙的aza-vinylogous Povarov 反应以顺序三组分方式进行。经过广泛的优化工作，该反应在以 20 Hz 运行的振动球磨机上进行，使用氧化锆球和球磨罐，并提供了在 C-2、C-4 以及在 C-6 处官能化的 1,2,3,4-四氢喹啉和 1,2,3,4-四氢-1,5-萘啶，在后一种情况下。该方案通常以良好到优异的收率和非对映选择性提供目标化合物。代表性实例的比较与在常规条件下获得的结果表明，机械化学方案在无溶剂环境中以可比收率提供更快的 Povarov 反应。
