93315-31-2Relevant academic research and scientific papers
Intramolecular cyclization of diarylmethanols and α,β-unsaturated amides promoted by KO: T -Bu/DMF: A metal-free approach towards 3,4-disubstituted quinolinones
Chen, Jia-Hua,Chen, Zi-Cong,Zhao, Hong,Zou, Yong,Zhang, Xue-Jing,Yan, Ming
, p. 11148 - 11153 (2016/12/07)
A facile synthesis of quinolinones through intramolecular addition of diarylmethanols to α,β-unsaturated amides promoted by KOt-Bu/DMF is reported. A series of 3,4-disubstituted quinolinones were obtained in moderate to good yields. A reaction pathway via the ketyl radical is proposed.
Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-α properties
Ribeiro, Nigel,Tabaka, Helena,Peluso, Jean,Fetzer, Ludivine,Nebigil, Can,Dumont, Serge,Muller, Christian D.,Desaubry, Laurent
, p. 5523 - 5524 (2008/03/13)
We synthesized 3-O-methylviridicatin 1 and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-α secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone 3 may provide the basis for the development of new anti-inflammatory agents.
Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines
Kadnikov, Dmitry V.,Larock, Richard C.
, p. 6772 - 6780 (2007/10/03)
The palladium-catalyzed annulation of internal alkynes by N-substituted o-iodoanilines under 1 atm of carbon monoxide results in the formation of 3,4-disubstituted 2-quinolones. The nature of the substituent on the nitrogen is crucial to obtaining high yields of 2-quinolones. The best results are obtained using alkoxycarbonyl, p-tolylsulfonyl, and trifluoroacetyl substituents. The nitrogen substituent is lost during the course of the reaction resulting in the formation of N-unsubstituted 2-quinolones. A variety of internal alkynes, bearing alkyl, aryl, heteroaryl, hydroxyl, and alkoxyl substituents, are effective in this process. Electron-rich and electron-poor N-substituted o-iodoanilines, as well as heterocyclic analogues, can be employed as annulating agents.
