Efficient Synthesis of Novel Quinolinone Derivatives via Catalyst-free Multicomponent Reaction

Author(s): Rui Du, Liangliang Han, Zhongqiang Zhou*, Victor Borovkov*.

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 5 , 2020

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Abstract:

The synthesis of 3-(aryl(piperidin-1-yl)methyl)-4-hydroxyquinolin-2(1H)-one derivatives via catalyst-free multicomponent reaction is described. The reaction of 4-hydroxyquinolin-2(1H)-one, piperidine, and 4-chlorobenzaldehyde was carried out in different solvents and under solvent-free conditions at room temperature. The best solvent in terms of the yield and reaction time was found to be dichloromethane. Most substituted benzaldehydes reacted with 4-hydroxyquinolin-2(1H)-one and piperidine to afford corresponding products in good-to-excellent yields. Aldehydes with electronwithdrawing groups were more reactive to exhibit higher reaction rates. However, 2-substituted benzaldehydes did not react with 4-hydroxyquinolin-2(1H)-one and piperidine under the reaction condition. Aldehydes bearing a hydroxyl group failed to produce the corresponding products.

Keywords: 4-hydroxyquinolin-2(1H)-one, aldehyde, piperidine, quinolinone derivatives, benzaldehydes, 2-chlorobenzaldehyde.

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Article Details

VOLUME: 17
ISSUE: 5
Year: 2020
Page: [403 - 407]
Pages: 5
DOI: 10.2174/1570178616666190828092728
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