Transition-Metal-Free One-Pot Tandem Synthesis of 4-Quinolone and 4H-Thiochromen-4-one Derivatives Through Sequential Nucleophilic Addition-Elimination-S_NAr Reaction

Deqiang Wang, Peng Sun, Peiyun Jia, Jinsong Peng*, Yixia Yue, Chunxia Chen*

*Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China, Email: jspeng1998nefu.edu.cn, ccx0109nefu.edu.cn

D. Wang, P. Sun, P. Jia, J. Peng, Y. Yue, C. Chen, Synthesis, 2017, 49, 4309-4320.

DOI: 10.1055/s-0036-1588466

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Abstract

4-Quinolones and 4H-thiochromen-4-ones are readily synthesized in a tandem one-pot manner from (Z)-β-chlorovinyl ketones in in good to excellent yields. An intermolecular nucleophilic addition of amines or sodium hydrogen sulfide to (Z)-β-chloro­vinyl ketones is followed by elimination of a chlorine anion to give a Z-enamine or thioenol intermediate, which gives the desired products through intramolecular S_NAr reaction.

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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

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

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Key Words

quinolones, 4H-thiochromen-4-ones, nucleophilic addition, elimination, S_NAr, tandem synthesis, transition-metal-free

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ID: J66-Y2017