87797-62-4Relevant articles and documents
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.
Aromatic Annelation by Reaction of Arylimidoyl Radicals with Alkynes: Evidence for the Intervention of a Spirocyclohexadienyl Radical in the Synthesis of Substituted Quinolines
Leardini, Rino,Nanni, Daniele,Pedulli, Gian Franco,Tundo, Antonio,Zanardi, Giuseppe
, p. 1591 - 1594 (2007/10/02)
Arylimidoyl radicals, generated by hydrogen abstraction from N-arylideneanilines with di-isopropyl peroxydicarbonate, react with alkynes to give quinolines in good yields.The reaction also involves an intermediate spirocyclohexadienyl radical; the proposed mechanism is discussed.
