10352-64-4Relevant academic research and scientific papers
A Heck reaction/photochemical alkene isomerization sequence to prepare functionalized quinolines
Donohoe, Timothy J.,Hoff, Oskar,Hoffman, Jack B.,Kelly, Alex,Walker, Johannes C. L.,Werrel, Simon
, (2020)
A route to prepare functionalized quinolines based on a Heck reaction/UV-induced alkene isomerization sequence is described. The method allows for the preparation of quinolines under mild and neutral conditions and has broad functional group tolerance. Acid-sensitive functional groups that would not be tolerated under previous approaches can be included and a one-pot quinoline forming procedure is also reported.
A Tf2O-Promoted Synthesis of Functionalized Quinolines from Ketoximes and Alkynes
Zheng, Weiping,Yang, Weiguang,Luo, Dongping,Min, Lin,Wang, Xinyan,Hu, Yuefei
supporting information, p. 1995 - 1999 (2019/03/13)
A new general synthesis of quinolines was developed from ketoximes and alkynes in the presence of Tf2O. It offered the first direct synthesis of quinolines by using the nitrilium salts generated in situ from a Tf2O-promoted Beckmann rearrangement of ketoximes under very easy conditions. (Figure presented.).
Metal-free synthesis of quinolines by direct condensation of amides with alkynes: revelation of N-aryl nitrilium intermediates by 2D NMR techniques
Ye, Jian-Liang,Zhu, Ya-Nan,Geng, Hui,Huang, Pei-Qiang
supporting information, p. 687 - 694 (2018/01/08)
Employing triflic anhydride/2-fluoropyridine as an activation system, the coupling reactions of secondary N-aryl amides with terminal alkynes yielded substituted quinolines in moderate to excellent yields. The reaction tolerated both electron-donating and electron-withdrawing groups at the benzamide moiety. Electron-rich aryl acetylenes served as excellent coupling partners, and aliphatic terminal alkynes such as cyclopropyl and conjugate vinyl acetylenes could also be used as reaction partners. By means of 2D NMR techniques (heteronuclear multiple bond correlation (HMBC), heteronuclear single quantum correlation (HSQC)), nitrilium ions were probed as reactive intermediates which are in contrast with that suggested by Movassaghi on the basis of in situ IR monitoring experiments. On the basis of these results, a plausible mechanism for the formation of quinolines was suggested.
