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

Add time:08/02/2019    Source:sciencedirect.com

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.

We also recommend Trading Suppliers and Manufacturers of 3-Phenylpropenoic acid 4-methylphenyl ester (cas 10519-07-0). Pls Click Website Link as below: cas 10519-07-0 suppliers

Prev:A Practical Synthesis of the Chronic Renal Disease Agent, 4,5-Dihydro-3H-1,4,8b-triazaacenaphthylen-3-one Derivatives, Using Regioselective Chlorination of Ethyl 5-methylimidazo[1,2-a]pyridine-3-carboxylate with N-Chlorosuccinimide
Next:Asymmetric synthesis of the β-amino acid methyl ester derivative of onchidin: (2S,3S)-methyl-3-amino-2-methyl-7-octynoate and its enantiomer)