Nghiên cứu tổng hợp các flavone mới trên cơ sở 2,4-dihydroxyacetophenone

Authors

  • Nguyễn Lê Anh
  • Trần Khắc Vũ

DOI:

https://doi.org/10.15625/4975

Keywords:

Claisen Schmidt, chalcone, 2, 4-dihydroxyacetophenone, flavone, propargyl bromide

Abstract

A series of new flavone derivatives (4a-g) was synthesized based on 2,4-dihydroxyacetophenone through a three-step procedure. Firstly, the reaction of 2,4-dihydroxyacetophenone (1) with propargyl bromide in acetone under reflux condition for 72 hours using K2CO3 as a catalyst gave the intermediate 2 in 75 % yield. Next, the Claisen Schmidt condensation reaction of 2 with different aldehydes in methanol in the presence of NaOH as a catalyst at room temperature obtained new chalcones 3a-g in 68-82 % yields. Finally, these chalcones were oxidatively cyclized in DMSO in the presence of I2 to furnish new flavones 4a-g in 45-59 % yields. The structure of synthesized compounds was elucidated using IR, NMR.

Keywords: Claisen Schmidt, chalcone, 2,4-dihydroxyacetophenone, flavone, propargyl bromide.

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Published

2014-09-17

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Section

Articles