Efficient construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides

Abstract

An efficient method for construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides has been developed. The practical approach is of excellent functional groups compatibility with as high as 98% yield under mild reaction conditions. Trapping and NMR analysis about the key intermediates of the transformation provided insights to propose a plausible mechanism for the intramolecular reductive cyclization. Moreover, further derivation successfully furnished hydroxyl substituted and N-methyl substituted derivatives which may provide a promising potential application in exploring biologically active compounds of 3-arylquinolin-4(1H)-ones.