Hydrogen Bond Assisted Three-Component Tandem Reactions to Access N-Alkyl-4-Quinolones

  • Molecules. 2023 Mar 2;28(5):2304. doi: 10.3390/molecules28052304.
Huanhuan Liu  1  2 ,  Huadan Liu  1  2 ,  Enhua Wang  3 ,  Liangqun Li  1  2 ,  Zhongsheng Luo  1  2 ,  Jiafu Cao  1  2 ,  Jialin Chen  1  2 ,  Lishou Yang  1  2 ,  Xiaosheng Yang  1  2
Affiliations
  • 1. State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China.
  • 2. The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, China.
  • 3. Department of Food and Medicine, Guizhou Vocational College of Agriculture, Qingzhen 551400, China.
PMID: 36903552 DOI: 10.3390/molecules28052304
Abstract

Hydrogen-bonding catalytic reactions have gained great interest. Herein, a hydrogen-bond-assisted three-component tandem reaction for the efficient synthesis of N-alkyl-4-quinolones is described. This novel strategy features the first proof of polyphosphate ester (PPE) as a dual hydrogen-bonding catalyst and the use of readily available starting Materials for the preparation of N-alkyl-4-quinolones. The method provides a diversity of N-alkyl-4-quinolones in moderate to good yields. The compound 4h demonstrated good neuroprotective activity against N-methyl-ᴅ-aspartate (NMDA)-induced excitotoxicity in PC12 cells.

Keywords
N-alkyl-4-quinolones; hydrogen bond; neuroprotective activity; polyphosphate ester; polyphosphoric acid.
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