Mild and direct conversion of quinoline N-oxides to 2-amidoquinolines with primary amides

Organic Letters
Michel CouturierTimothy D White

Abstract

[reaction: see text] A simple, one-pot procedure is described for the direct conversion of quinoline N-oxides to alpha-amidoquinolines with primary amides. This methodology is complimentary to the Abramovich reaction, which is limited to the introduction of secondary amides via imidoyl chlorides. Although reaction conditions are quite similar, omission of the base is key for successful reaction with primary amides, which were found not to proceed through the intermediacy of an imidoyl chloride but rather through an acyl isocyanate.

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Citations

Jan 7, 2017·The Journal of Organic Chemistry·Ya-Ping HanYong-Min Liang
Aug 20, 2015·Organic & Biomolecular Chemistry·Rafał Loska, Patrycja Bukowska
Mar 20, 2014·Organic & Biomolecular Chemistry·Oleg V LarionovBehije Skenderi
Apr 3, 2020·Organic & Biomolecular Chemistry· RituNidhi Jain
Apr 1, 2020·Organic & Biomolecular Chemistry·Jin-Wei YuanLing-Bo Qu
Mar 18, 2021·Beilstein Journal of Organic Chemistry·Geetanjali S SontakkeChandra M R Volla
Dec 31, 2008·The Journal of Organic Chemistry·Jonathan William Medley, Mohammad Movassaghi
May 16, 2007·The Journal of Organic Chemistry·Jingjun YinIan W Davies
Jan 11, 2018·Organic Letters·Sergei A ShipilovskikhAndrei V Malkov
Sep 4, 2021·Journal of the American Chemical Society·Jeffrey M Lipshultz, Alexander T Radosevich

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