Journal of Organic Chemistry p. 6563 - 6572 (2016)
Update date:2022-08-11
Topics:
Saunthwal, Rakesh K.
Patel, Monika
Verma, Akhilesh K.
A highly efficient metal and protection-free approach for the regioselective synthesis of C-3-functionalized quinolines from azadienes (in situ generated from 2-aminobenzyl alcohol) and terminal alkynes through [4 + 2] cycloaddition has been developed. An unprecedented reaction of 2-aminobenzyl alcohol with 1,3- and 1,4-diethynylbenzene provided the C-3 tolylquinolines via [4 + 2] HDA and oxidative decarboxylation. The -NH2 group directed mechanistic approach was well supported by the control experiments and deuterium-labeling studies and by isolating the azadiene intermediate. The reactivity and selectivity of unprotected azadiene in metal-free base-assisted hetero-Diels-Alder reaction is exploited to quickly assemble an important class of C-3-functionalized quinolines, which are difficult to access.
View MoreContact:+852-8198 2399
Address:9E, Leapont Industrial Building, 18-28 Wo Liu Hang Road, Shatin, New Territories, Hong Kong
website:http://www.fwdchem.com
Contact:86-21-54450828
Address:Room 802,Lotus Tower ,159 Tianzhou Road,Xuhui District,Shanghai
Shanghai Dianyang Industry Co.,ltd
Contact:+86 21 6492 4669
Address:Chejing RD, Songjiang District, Shanghai, China
Contact:(1) 206-3550089
Address:5115 NE 8TH PL, Renton, WA 98059 USA
GUANGZHOUGRENSPSPORTS FACILITIES CO LTD
Contact:
Address:
Doi:10.1021/acs.jmedchem.6b01468
(2017)Doi:10.1002/cctc.201300785
(2014)Doi:10.1021/ja01280a033
()Doi:10.1142/S1088424616501030
(2016)Doi:10.1002/macp.1978.021790814
(1978)Doi:10.1007/BF00622239
(1958)