Petersen Wade F, Taylor Richard J K, Donald James R
Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
Org Biomol Chem. 2017 Jul 21;15(27):5831-5845. doi: 10.1039/c7ob01274h. Epub 2017 Jun 30.
A reductive approach for carbamoyl radical generation from N-hydroxyphthalimido oxamides under photoredox catalysis is outlined. This strategy was applied to the synthesis of 3,4-dihydroquinolin-2-ones via the intermolecular addition/cyclization of carbamoyl radicals with electron deficient olefins in a mild, redox-neutral manner. Under a general set of reaction conditions, diversely substituted 3,4-dihydroquinolin-2-ones, including spirocyclic systems can be prepared. By using chlorine-substituted olefins, aromatic quinolin-2-ones can also be accessed.
概述了一种在光氧化还原催化下由N-羟基邻苯二甲酰亚胺草酰胺生成氨基甲酰基自由基的还原方法。该策略以温和、氧化还原中性的方式通过氨基甲酰基自由基与缺电子烯烃的分子间加成/环化反应应用于3,4-二氢喹啉-2-酮的合成。在一般的反应条件下，可以制备各种取代的3,4-二氢喹啉-2-酮，包括螺环体系。通过使用氯取代的烯烃，也可以得到芳族喹啉-2-酮。
