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

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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.

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Acknowledgements

The present work was supported by the National Natural Science Foundation of China (Nos. 20872118, 30070905) and the Natural Science Foundation of the Science and Technology Department of Shaanxi Province (2014JM4097).

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Correspondence to Xuejun Wang.

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Wang, X., Liu, J., Zhang, Y. et al. An efficient one-pot synthesis of 4′-substituted flavones. Chem. Pap. 72, 229–233 (2018). https://doi.org/10.1007/s11696-017-0275-8

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  • DOI: https://doi.org/10.1007/s11696-017-0275-8

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