Base-Promoted Carbocyclization Reactions of alpha-Substituted N-(2-Alkynylphenyl) acetamides

作者：Chen Yan Jhu; Chuang Che Ping

来源：Synthesis (Germany), 2016, 48(20): 3603-3617.

DOI：10.1055/s-0035-1562434

• copper salts
• oxidative
• carbocyclization
• 2-alkynylarylamines
• quinolin-2(1H)-ones

A synthetic method for highly functionalized quinolin-2(1H)-ones has been developed. The copper(II) chloride-catalyzed aerobic oxidative carbocyclization reactions of alpha-substituted N-[2-(phenylethynyl) phenyl] acetamides, via the Conia-ene-type intramolecular carbocupration onto the alkynyl moiety, produced 3,4-difunctionalized quinolin-2(1H)-ones. In the absence of copper(II) chloride, these a-substituted acetamides undergo base-promoted nucleophilic 6-exo-dig carbocyclization to generate 3-functionalized quinolin-2(1H)-ones. Several useful functional groups including benzoyl, alkanoyl, diethoxyphosporyl, cyano, and methoxycarbonyl groups are compatible with the reaction conditions. a-Substituted N-(2-ethynylphenyl) acetamides bearing a terminal C C bond could also be used to generate the corresponding 4-methyl-substituted quinolin-2(1H)-ones smoothly.

• 出版日期2016-10