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An efficient one-pot synthesis of 4′-substituted flavones

Xuejun Wang, Jianli Liu, Yilin Zhang, and Xuhua Liang

Shangluo University, Shangluo, China

 

E-mail: xuejunwangd@163.com

Abstract: A series of flavones were synthesized from 2-hydroxyacetophenones using a modified Baker–Venkataraman reaction. The 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone, or 2,5-dihydroxyacetophenone, or 2,6-dihydroxyacetophenone was treated with 2 equiv of a 4-substituted aroyl chloride in 99:1 (w/w) acetone/water using both K2CO3 (8 equiv) and pyridine (4 equiv) as bases. Various 4′-substituted (R=H, Me, Cl, F) flavone derivatives were obtained via this one-pot procedure in high yield (≥70%). This modified process is both simple and efficient. Compound 26b (3-(4-fluorobenzoyl)-5-hydroxy-4′-fluoroflavone) was synthesized for the first time with a yield of 12%. The method was unsuccessful, however, for the synthesis of one flavone, 5-hydroxy-4′-methoxyflavone.

Keywords: Flavone derivatives ; Synthesis ; Baker–Venkataraman 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0275-8

 

Chemical Papers 72 (1) 229–233 (2018)

Saturday, May 30, 2020

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