Synthesis of 1,4-dihydroquinoline derivatives under transition-metal-free conditions and their diverse applications.
A transition-metal-free process for the synthesis of 1,4-dihydroquinoline derivatives starting from simple enaminones with aldehydes via intermolecular cascade cyclization in a one-pot protocol is developed. This methodology affords a variety of products in moderate to good yields. Particularly, the use of the enaminone fragment in 1,4-dihydroquinoline derivatives 3 as a leaving group for further diverse applications with C-nucleophiles is proved to be feasible.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou, 215123, People's Republic of China. xuxp@suda.edu.cn shunjun@suda.edu.cn.
Xue-Qiang
XQ
Chu
You
Y
Zi
Hua
H
Meng
Xiao-Ping
XP
Xu
Shun-Jun
SJ
Ji
D002384:Catalysis; D007211:Indoles / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D009595:Nitroparaffins / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D028561:Transition Elements / Q000737:chemistry*
C544515:1,4-dihydroquinoline; D007211:Indoles; D009595:Nitroparaffins; D011804:Quinolines; D028561:Transition Elements; D008697:Methane; C008640:nitromethane