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

Author:
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.
Source:
Journal of organic chemistry 2018 v.83 no.21 pp. 13132-13145
ISSN:
1520-6904
Subject:
Penicillium, aldehydes, alkylation, chemical structure, epoxidation reactions, fungi, metabolites, organic chemistry
Abstract:
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.
Agid:
6194445