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Synthesis 2017; 49(18): 4309-4320
DOI: 10.1055/s-0036-1588466
paper
© Georg Thieme Verlag Stuttgart · New York

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

Deqiang Wang
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. China   Email: jspeng1998@nefu.edu.cn   Email: ccx0109@nefu.edu.cn
,
Peng Sun
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. China   Email: jspeng1998@nefu.edu.cn   Email: ccx0109@nefu.edu.cn
,
Peiyun Jia
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. China   Email: jspeng1998@nefu.edu.cn   Email: ccx0109@nefu.edu.cn
,
Jinsong Peng  *
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. China   Email: jspeng1998@nefu.edu.cn   Email: ccx0109@nefu.edu.cn
,
Yixia Yue
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. China   Email: jspeng1998@nefu.edu.cn   Email: ccx0109@nefu.edu.cn
,
Chunxia Chen*
Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. China   Email: jspeng1998@nefu.edu.cn   Email: ccx0109@nefu.edu.cn
› Author Affiliations31300286
We are grateful for the financial support from the Fundamental Research Funds for the Central Universities (2572015EB02) and the National Natural Science Foundation of China (31400294 and 31300286).
Further Information

Publication History

Received: 02 April 2017

Accepted after revision: 24 May 2017

Publication Date:
19 July 2017 (online)

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Abstract

4-Quinolone and 4H-thiochromen-4-one derivatives are readily synthesized in a tandem one-pot manner in good to excellent yields. Starting from (Z)-β-chlorovinyl ketones, an intermolecular nucleo­philic addition of amines or sodium hydrogen sulfide to (Z)-β-chloro­vinyl ketones was followed by elimination of chlorine anion to give Z-enamine or thioenol intermediates, which can be transformed to 4-quinolone or 4H-thiochromen-4-one products through intramolecular SNAr reaction, respectively.

Key words

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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588466.
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