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One-Pot Synthesis of Quinolin-4(1H)-one Derivatives by a Sequential Michael Addition-Elimination/Palladium-Catalyzed Buchwald-Hartwig Amination Reaction

Yinghua Wang, Hanyu Liang, Chunxia Chen*, Deqiang Wang, Jinsong Peng*

*Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China, Email: jspeng1998nefu.edu.cn, 080122nefu.edu.cn

Y. Wang, H. Liang, C. Chen, D. Wang, J. Peng, Synthesis, 2015, 47, 1851-1860.

DOI: 10.1055/s-0034-1380496 (free Supporting Information)


Abstract

Intermolecular Michael addition of an amine to a (Z)-β-chlorovinyl ketone followed by elimination of a chloride anion provides enamine intermediates, with full retention of the initial Z-configuration. These intermediates can be transformed into quinolin-4(1H)-one products by a palladium-catalyzed intramolecular N-arylation in a tandem one-pot manner, with good to excellent yields.

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Key Words

4-quinolones, ketones, Michael additions, aminations, tandem reactions, cyclizations


ID: J66-Y2015