Superelectrophilic activation of N-aryl amides of 3-arylpropynoic acids: synthesis of quinolin-2(1H)-one derivatives

作者：Ryabukhin Dmitry S; Gurskaya Larisa Yu; Fukin Georgy K; Vasilyev Aleksander V^*

来源：Tetrahedron, 2014, 70(37): 6428-6443.

DOI：10.1016/j.tet.2014.07.028

• N-Aryl amides of 3-arylpropynoic acids
• 4-Aryl quinolin-2(1H)-ones
• 4,4-Diaryl-3,4-dihydroquinolin-2-(1H)-ones
• Superacids
• Superelectrophilic activation

The superelectrophilic activation of N-aryl amides of 3-arylpropynoic acids by Bronsted superacids (CF3SO3H, HSO3F) or strong Lewis acids AlX3 (X=Cl, Br) results in the formation of 4-aryl quinolin-2(1H)-ones in quantitative yields. The vinyl triflates or vinyl chlorides may be formed as additional reaction products. The investigated amides in reactions with benzene give 4,4-diaryl 3,4-dihydroquinolin-2-(1H)-ones under the superelectrophilic activation. 4-Aryl quinolin-2(1H)-ones in POCl3 are converted into 4-aryl 2-chloroquinolines. 4-Fluoropheny1-4-phenyl 3,4-dihydroquinolin-2-(1H)-one give N-formylation products in a yield of 79% under the Vilsmeier-Haack reaction conditions.

• 出版日期2014-9-16