Chen Lin, Liang Wei
School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001, P. R. of China.
Org Biomol Chem. 2022 Apr 13;20(15):3201-3210. doi: 10.1039/d2ob00096b.
Michael/ammonolysis cascade reactions between cyclohexane-1,3-dione-derived enaminones and olefinic azlactones phase-transfer catalysis have been developed. This method provides rapid access to a suite of architecturally complex and diverse quinoline-2,5-diones bearing a secondary amide group at the C-3 position in moderate to excellent yields (53-94%) and with excellent diastereoselectivities (>99 : 1 dr in most cases). The achievement of a preparative-scale reaction and the diverse product derivatization that can be obtained highlight the application potential of this protocol both in academic and industrial settings. An investigation of the reaction mechanism implies that tetrabutylammonium hydroxide may be the actual catalyst during this cascade reaction.
已开发出环己烷-1,3-二酮衍生的烯胺酮与烯属恶唑烷酮之间的迈克尔/氨解级联反应及相转移催化。该方法能快速获得一系列结构复杂多样的喹啉-2,5-二酮，这些产物在C-3位带有仲酰胺基团，产率适中至优异（53-94%），且具有优异的非对映选择性（大多数情况下>99:1 dr）。制备规模反应的实现以及可获得的多样产物衍生化突出了该方案在学术和工业环境中的应用潜力。对反应机理的研究表明，氢氧化四丁铵可能是该级联反应中的实际催化剂。
