37612-62-7Relevant academic research and scientific papers
Visible-Light-Induced Synthesis of 1,2,3,4-Tetrahydroquinolines through Formal [4+2] Cycloaddition of Acyclic α,β-Unsaturated Amides and Imides with N,N-Dialkylanilines
Itoh, Kennosuke,Nagao, Shun-ichi,Tokunaga, Ken,Hirayama, Shigeto,Karaki, Fumika,Mizuguchi, Takaaki,Nagai, Kenichiro,Sato, Noriko,Suzuki, Mitsuaki,Hashimoto, Masashi,Fujii, Hideaki
, p. 5171 - 5179 (2021)
1,2,3,4-Tetrahydroquinolines should be applicable to the development of new pharmaceutical agents. A facile synthesis of 1,2,3,4-tetrahydroquinolines that is achieved by a photoinduced formal [4+2] cycloaddition reaction of acyclic α,β-unsaturated amides and imides with N,N-dialkylanilines under visible-light irradiation, in which a new IrIII complex photosensitizer, a thiourea, and an oxidant act cooperatively in promoting the reaction, is reported. The photoreaction enables the synthesis of a wide variety of 1,2,3,4-tetrahydroquinolines, while controlling the trans/cis diastereoselectivity (>99:1) and constructing contiguous stereogenic centers. A chemoselective cleavage of an acyclic imide auxiliary is demonstrated.
