Simple synthesis of 3-hydroxyquinolines via Na2S2O4-mediated reductive cyclization of (2-(2-nitrophenyl)oxiran-1-y1)(aryl) methanones (o-nitrobenzalacetophenone oxides)

摘要

An efficient sodium dithionite (Na2S2O4)-mediated method for construction of 3-hydroxyquinolines via in situ Meinwald rearrangement/intramolecular reductive cyclization of o-nitrobenzalacetophenone oxides has been developed. The practical approach is of excellent functional group compatibility with as high as 98% yield under mild reaction conditions. Moreover, further manipulation successfully furnished 4-bromo substituted derivatives which may provide a promising potential application in exploring biologically active analogs of 3-hydroxyquinolines. (C) 2017 Elsevier Ltd. All rights reserved.