Tetrahedron p. 3273 - 3282 (1996)
Update date:2022-08-03
Topics:
Strekowski, Lucjan
Janda, Lubomir
Patterson, Steven E.
Nguyen, Johnny
The title ketimines containing a fluorine atom at position 2 of the phenyl group are efficiently cyclized under mild conditions to N-[2-(dimethylamino)ethyl]-2-(2-fluorophenyl)quinolin-4-amines by the reaction with a lithium reagent derived from N,N-dimethylethylenediamine. The facile regioselective displacement of C2-F in the presence of another fluorine atom at the phenyl group by the same reagent or N-lithio-N'-methylpiperazide at a higher temperature is explained in terms of a complex induced proximity effect (CIPE) process. The CIPE process is operative in amination of the 2-fluoro-phenyl ketimines by the more reactive piperazide reagent prior cyclization to quinolines. The 2-chloro-phenyl derivatives are much less reactive in the CIPE assisted amination.
View MoreContact:+852-8198 2399
Address:9E, Leapont Industrial Building, 18-28 Wo Liu Hang Road, Shatin, New Territories, Hong Kong
Suzhou CarbonWell Pharma-Tech Co., Ltd
Contact:Tel: + 86 (0)512-8898-1216; + 86-18606258602
Address:2358 Changan Road, Wujiang Scientific Innovation Park, Wujiang, Jiangsu Province, P. R. China 215200
Shanghai ZaiQi Bio-Tech Co., Ltd.,
Contact:+86-21-5482 4098
Address:Bldg. No.7, No.201 MinYi Rd,Songjiang CaoHeJing High-Tech Park Shanghai 201516 P,R,China
Jinzhou Jiutai Pharmaceutical Co.,Ltd
Contact:+86-0416-5179890
Address:No.41, Taianli, Taihe District, Jinzhou, Liaoning
Shanghai Sunwise Chemical Co., Ltd
website:http://www.sunwisechem.com
Contact:86-021-33883180
Address:Room 10E, Building G, Westlink Center, No. 2337 Gudai Road, Minhang District, Shanghai, China PC: 201100
Doi:10.1016/S0040-4020(97)00769-2
(1997)Doi:10.3390/molecules13020340
(2008)Doi:10.1021/jo01275a055
(1968)Doi:10.1016/0040-4039(96)00200-6
(1996)Doi:10.1021/ja953470f
(1996)Doi:10.1039/cc9960000779
(1996)