Synthesis of 3‑Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

Mamedov, Vakhid A.; Mamedova, Vera L.; Kadyrova, Saniya F.; Galimullina, Venera R.; Khikmatova, Gul’naz
Z.; Korshin, Dmitry E.; Gubaidullin, Aidar T.; Krivolapov, Dmitry B.; Rizvanov, Il’dar Kh.; Bazanova, Olga B.; Sinyashin, Oleg G.; Latypov, Shamil K.

doi:10.1021/acs.joc.8b01871.s001

Synthesis of 3‑Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

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posted on 2018-10-01, 00:00 authored by Vakhid A. Mamedov, Vera L. Mamedova, Saniya F. Kadyrova, Venera R. Galimullina, Gul’naz Z. Khikmatova, Dmitry E. Korshin, Aidar T. Gubaidullin, Dmitry B. Krivolapov, Il’dar Kh. Rizvanov, Olga B. Bazanova, Oleg G. Sinyashin, Shamil K. Latypov

The new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones through the Darzens condensation (epoxidation) of dichloroacetanilides with aromatic aldehydes followed by one-pot dechlorative epoxide-arene cyclization is described. This methodology has been utilized for the synthesis of naturally occurring viridicatol, a fungal metabolite isolated from the penicillium species.

Synthesis of 3‑Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

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