Citation: Chen Xuebing, Bai Hairui, Huang Chao. Concise Synthesis of Quinolinone Derivatives[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 881-888. doi: 10.6023/cjoc201611003 shu

Concise Synthesis of Quinolinone Derivatives

Chen Xuebing ^a,*,, ,
Bai Hairui ^b ,
Huang Chao ^b,*,,

a.
Key Laboratory of Natural Pharmaceutical and Chemical Biology of Yunnan Province, School of Science, Honghe University, Mengzi 661100
b.
Engineering Research Center of Biopolymer Functional Materials of Yunnan Province, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650503

Corresponding author: Chen Xuebing, orangekaka@126.com Huang Chao, huang.chao@hotmail.com
Received Date: 1 November 2016
Revised Date: 27 December 2016

Fund Project: the National Natural Science Foundation of China 21662046the National Natural Science Foundation of China 21202142the Yunnan Provincal Department of Education Fund 2016ZZX217

Figures(3)

A concise and efficient protocol for the synthesis of novel quinolinone derivatives 4 has been established from a intramolecular cyclization of cyanoacetylenaminones 3, which were synthesized by the regio-selective cyanoacylation reaction of β-enaminones 1 with cyanoacetic acid 2. The reaction was performed in acetonitrile media at 40 ℃, and piperidine as catalyst. As a result, a novel series of quinolinones 4a~4t were obtained with the yields of 82%~95%. The reaction is particularly attractive due to the following advantages of operational simplicity, atom economy, simple starting materials, and easy purification.
- β-enaminones,
- regionselectivity acylation,
- intramolecular cyclization,
- quinolinones
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