A ONE-POT APPROACH TO CONSTRUCT 3-(2-METHOXYPYRIDIN-3-YL)-4H-CHROMEN-4-ONES VIA MEINWALD REARRANGEMENT/INTRAMOLECULAR DEMETHYLATION ANNULATION OF EPOXIDES

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.

Automated summary

A convenient method for constructing 3-(2-methoxypyridin-3-yl)-4H-chromen-4-ones has been successfully developed, with high yields and good functional group compatibility. Further derivatization was achieved through Suzuki-Miyaura cross-coupling reaction, potentially opening up new possibilities for exploring the biological activity of these compounds.