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

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

doi:10.1021/acs.joc.8b01871

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

J Org Chem. 2018 Nov 2;83(21):13132-13145. doi: 10.1021/acs.joc.8b01871. Epub 2018 Oct 17.

Authors

Vakhid A Mamedov^{1

2}, Vera L Mamedova^{1

2}, Saniya F Kadyrova^{1

2}, Venera R Galimullina¹, Gul'naz Z Khikmatova^{1

2}, Dmitry E Korshin^{1

2}, Aidar T Gubaidullin¹, Dmitry B Krivolapov¹, Il'dar Kh Rizvanov¹, Olga B Bazanova¹, Oleg G Sinyashin², Shamil K Latypov¹

Affiliations

¹ A.E. Arbuzov Institute of Organic and Physical Chemistry , FRC Kazan Scientific Center of Russian Academy of Sciences , Arbuzov str. 8 , 420088 Kazan , Russian Federation.
² Kazan National Research Technological University , Karl Marx str. 68 , 420015 Kazan , Russian Federation.

PMID: 30272451
DOI: 10.1021/acs.joc.8b01871

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.

Publication types

Research Support, Non-U.S. Gov't