TY - JOUR
T1 - Base-Promoted Carbocyclization Reactions of α-Substituted N-(2-Alkynylphenyl)acetamides
AU - Chen, Yan Jhu
AU - Chuang, Che Ping
N1 - Publisher Copyright:
© Georg Thieme VerlagStuttgart · New York.
PY - 2016/10/17
Y1 - 2016/10/17
N2 - A synthetic method for highly functionalized quinolin-2(1H)-ones has been developed. The copper(II) chloride-catalyzed aerobic oxidative carbocyclization reactions of α-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 α-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. α-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.
AB - A synthetic method for highly functionalized quinolin-2(1H)-ones has been developed. The copper(II) chloride-catalyzed aerobic oxidative carbocyclization reactions of α-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 α-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. α-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.
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U2 - 10.1055/s-0035-1562434
DO - 10.1055/s-0035-1562434
M3 - Article
AN - SCOPUS:84976328588
SN - 0039-7881
VL - 48
SP - 3603
EP - 3617
JO - Synthesis (Germany)
JF - Synthesis (Germany)
IS - 20
ER -