Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines

The Journal of Organic Chemistry
Dmitry V Kadnikov, Richard C Larock

Abstract

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.

Citations

Oct 4, 2013·Chemical & Pharmaceutical Bulletin·Kiyofumi Inamoto
Feb 17, 2015·The Journal of Organic Chemistry·Weiguo WangZhenghu Xu
Jul 18, 2015·Journal of the American Chemical Society·Xinyao LiNing Jiao
Sep 29, 2011·The Journal of Organic Chemistry·Noriko OkamotoReiko Yanada
Jun 22, 2011·Journal of the American Chemical Society·Kenichiro NakaiSeijiro Matsubara
Jun 30, 2010·Journal of the American Chemical Society·Tomohiro IwaiYasushi Tsuji
Jan 29, 2013·Organic Letters·Kenichiro NakaiSeijiro Matsubara
Oct 9, 2012·Chemical Reviews·Xiao-Feng WuMatthias Beller
Jan 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Vera L M Silva, Artur M S Silva
Mar 7, 2019·Chemistry : a European Journal·Ji-Wei RenHua Yang
Oct 11, 2017·Chemical Science·Xinyao LiNing Jiao
Nov 26, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wan Pyo HongHee Nam Lim
May 8, 2010·The Journal of Organic Chemistry·Kiyofumi InamotoTakayuki Doi
Apr 17, 2008·Journal of the American Chemical Society·Yuichi KajitaTakuya Kurahashi
Feb 28, 2007·Journal of Medicinal Chemistry·Christian PeiferStefan Laufer
Aug 26, 2010·Journal of Medicinal Chemistry·Doris RietherDavid S Thomson
Oct 27, 2006·The Journal of Organic Chemistry·Raymond J CvetovichJennifer R Chilenski

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