Simple synthesis of 3-hydroxyquinolines via Na2S2O4-mediated reductive cyclization of (2-(2-nitrophenyl)oxiran-1-yl)(aryl)methanones (o-nitrobenzalacetophenone oxides)
2017
Mamedov, Vakhid A. | Mamedova, Vera L. | Syakaev, Victor V. | Korshin, Dmitry E. | Khikmatova, Gul'naz Z. | Mironova, Ekaterina V. | Bazanova, Olga B. | Rizvanov, Il'dar Kh | Latypov, Shamil K.
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.
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