Palladium-catalyzed intermolecular aerobic oxidative cyclization of 2-ethynylanilines with isocyanides: regioselective synthesis of 4-halo-2-aminoquinolines.
A robust and regioselective palladium-catalyzed intermolecular aerobic oxidative cyclization of 2-ethynylanilines with isocyanides to the synthesis of 4-halo-2-aminoquinolines is reported herein. The procedure constructs various 4-halo-2-aminoquinolines with moderate to excellent yields (47-94%) and broad substrates scope. Furthermore, this process can be easily extended to synthesis of various 6H-indolo[2,3-b]quinolines via an intramolecular Buchwald-Hartwig cross-coupling reaction in two-step one-pot manner.
School of Chemistry and Chemical Engineering, South China University of Technology , Guangzhou, Guangdong 510640, PR China.
Bifu
B
Liu
Hanling
H
Gao
Yue
Y
Yu
Wanqing
W
Wu
Huanfeng
H
Jiang
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
C483919:2-ethynylaniline; D000634:Aminoquinolines; D000814:Aniline Compounds; D003486:Cyanides; D010165:Palladium; D000114:Acetylene