通过分子内铜催化的 C-H 官能化/C-N 键形成反应，从 3,3-二芳基丙烯酰胺中得到 4-芳基-2-喹诺酮。
4-Aryl-2-quinolones from 3,3-diarylacrylamides through intramolecular copper-catalyzed C-H functionalization/C-N bond formation.
机构信息
Dipartimento di Chimica e Tecnologie del Farmaco, La Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, Italy.
出版信息
J Org Chem. 2012 Mar 2;77(5):2537-42. doi: 10.1021/jo202427m. Epub 2012 Feb 22.
PMID:22283237
Abstract
Free NH 3,3-diarylacrylamides are cyclized to substituted 2-quinolones in the presence of CuI, PPh(3), and KO-t-Bu in o-xylene at 100 °C. The reaction proceeds through a C-H functionalization/C-N bond formation process. With unsymmetrical 3,3-diarylacrylamides, high selectivity is observed using substrates where the aromatic ring trans to the amide group bears o-methyl, -chloro, or -bromo substituents.
摘要
游离的 3,3-二芳基丙烯酰胺在碘化亚铜、三苯基膦和叔丁醇钾存在下，在 100°C 的二甲苯中环化生成取代的 2-喹诺酮。该反应通过 C-H 官能化/C-N 键形成过程进行。对于不对称的 3,3-二芳基丙烯酰胺，当酰胺基团的邻位芳环带有 o-甲基、-氯或 -溴取代基时，反应表现出较高的选择性。
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