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Short Paper | Regular issue | Vol 102, No. 6, 2021, pp.1194-1209
Published online, 12th April, 2021
DOI: 10.3987/COM-21-14459
A One-Pot Approach to Construct 3-(2-Methoxypyridin-3-yl)-4H-chromen-4-ones via Meinwald Rearrangement/Intramolecular Demethylation Annulation of Epoxides

Min-Qi Hu, Ying Zhang, Kai-Li Dai, Li-Fang Yu, Ting Liu, Jie Tang, and Fan Yang*

*Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, PR China


A convenient and practical approach for construction of 3-(2-methoxypyridin-3-yl)-4H-chromen-4-ones has been successfully developed by a one-pot Meinwald rearrangement/intramolecular demethylation annulation reaction sequence with easily accessible epoxides as the starting material. The synthetic protocol is of excellent functional group compatibility under mild reaction conditions, and 3-(2-methoxypyridin-3-yl)-4H-chromen-4-ones were obtained in high yields. Moreover, further derivation successfully furnished more complicated derivatives by Suzuki-Miyaura cross-coupling reaction which may provide a promising potential application in exploring biological activity of 3-aryl-4H-chromen-4-ones.