Journal of Organic Chemistry p. 9993 - 10006 (2020)
Update date:2022-08-05
Topics:
Muzalevskiy, Vasiliy M.
Belyaeva, Kseniya V.
Trofimov, Boris A.
Nenajdenko, Valentine G.
The reaction of quinolines with CF3-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The decisive role of the base in the reaction direction was shown. Using these reactions, highly efficient pathways to 2-arylquinolines and 2-aryl-3-trifluoroacetylquinolines were elaborated to provide the corresponding compounds in high yields using a simple one-pot procedure. The possible mechanism of rearrangement is discussed.
View MoreChengdu CSH Pharmaceutical Co.,ltd
Contact:+86-(28)-85321971
Address:Block B,New Hope Int. Tian Fu New District, Chengdu, Sichuan, China
China Synchem Technology Co.,Ltd
website:http://www.cnsynchem.com
Contact:+86-0552-4929311
Address:No.217 Daqing Road
Shanghai Rainbow Chemistry Co., Ltd.
Contact:+86-21-64968086-5815/5812
Address:3rd floor, Building 7, 251 Faladi Road, Zhangjiang Hi-Tech Park, Pudong District, Shanghai, P.R. China
Shangyu Sanhechemicals Co.,LTD.
Contact:86-0571-56696839
Address:Num.2952,Nanhuan Road,Binjiang District,Hangzhou,China
Jiaozuo Zhongwei Special Products Pharmaceutical Co.,Ltd.
website:http://www.zw-pvp.com
Contact:15302105619
Address:Jiaozuo,Henan,China (Mainland)
Doi:10.1021/jo00019a053
(1991)Doi:10.1021/ma202168m
(2012)Doi:10.1055/s-0030-1260177
(2011)Doi:10.1016/j.bcp.2011.10.004
(2012)Doi:10.1080/00397911.2010.541966
(2012)Doi:10.1007/BF00633218
(1991)