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.
References
Baker W (1933) Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones. J Chem Soc 8:1381–1389. doi:10.1039/JR9330001381
Bois F, Beney C, Mariotte AM, Boumendjel A (1999) A one-step synthesis of 5-hydroxyflavones. Synlett 11(9):1480–1482. doi:10.1055/s-1999-2844
Chee CF, Buckle MJC, Rahman NA (2011) An efficient one-pot synthesis of flavones. Tetrahedron Lett 52(4):3120–3123. doi:10.1016/j.tetlet.2011.04.022
Franco C, Rossella F, Adriana B, Paola C, Daniela S, Francesca R (2010) A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors. Bioorg Med Chem 18(3):1273–1279. doi:10.1016/j.bmc.2009.12.029
Ganguly AK, Kaur S, Mahata PK, Biswas D, Pramanik BN, Chan TM (2005) Synthesis and properties of 3-acyl-c-pyrones, a novel class of flavones and chromones. Tetrahedron Lett 46(4):4119–4121. doi:10.1016/j.tetlet.2005.04.010
Ganguly AK, Mahata PK, Biswas D (2006) Synthesis of oxygen heterocycles. Tetrahedron Lett 47(12):1347–1349. doi:10.1016/j.tetlet.2005.12.062
Jae IL, Hwa SS, Mi GJ (2005) A novel synthesis of flavones from 2-methoxybenzoic acids. Bull Korean Chem Soc 26(9):1461–1463. doi:10.1002/chin.200607144
Jiraporn U, Chanpen W, Weerasak S, Patcharawee N, Narumol P (2011) Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor. J Mol Struct 1001(1–3):152–161. doi:10.1016/j.molstruc.2011.06.035
Masato M, Masaki T, Ayano T, Takahide T, Hiroto T, Takayuki S (2010) An effective synthesis of 5,4′-disubstituted flavones via a cesium enolate assisted intramolecular ipso-substitution reaction. Chem Pharma Bull 58(8):1107–1110. doi:10.1248/cpb.58.1107
Pinto DCGA, Silva Artur MS, Almeida Lucia MPM, Cavaleiro Jose AS, Elguero J (2002) 3-Aroyl-5-hydroxyflavones: synthesis and transformation into aroylpyrazoles. Eur J Org Chem 22:3807–3815. doi:10.1002/1099-0690(200211)2002:22<3807:AID-EJOC3807>3.0.CO;2-2
Wang XJ, Liu JL (2014) Synthesis and preliminary antitumor activities of 7(6)-hydroxy flavone derivatives. Chin J Org Chem 34(08):1609–1615. doi:10.6023/cjoc201402013
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).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-017-0275-8