Details

Autor(en) / Beteiligte

• Ryabukhin, Dmitry S.
• Gurskaya, Larisa Yu
• Fukin, Georgy K.
• Vasilyev, Aleksander V.

Titel

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

Ist Teil von

• Tetrahedron, 2014-09, Vol.70 (37), p.6428-6443

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2014

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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-Fluorophenyl-4-phenyl 3,4-dihydroquinolin-2-(1H)-one give N-formylation products in a yield of 79% under the Vilsmeier–Haack reaction conditions. [Display omitted]