An efficient and scalable synthesis of substituted phenanthrenequinones by intramolecular Friedel-Crafts reaction of imidazolides.
Org Lett
; 9(21): 4103-6, 2007 Oct 11.
Article
em En
| MEDLINE
| ID: mdl-17880225
ABSTRACT
An efficient synthesis of 9,10-phenanthrenequinones is described. The two carbonyl groups were introduced by an orthoselective intermolecular Friedel-Crafts reaction of 3-methoxyphenol with ethyl chlorooxoacetate. The formation of a biaryl bond by Suzuki-Miyaura coupling reaction, followed by the hydrolysis of the ester, gave a biaryloxoacetic acid. Treatment of this acid with CDI gave the corresponding imidazolide. The ring closure to the desired phenanthrenequinone was accomplished by intramolecular Friedel-Crafts reaction of the imidazolide promoted by TiCl(4).
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Fenantrenos
/
Quinonas
/
Imidazóis
Idioma:
En
Ano de publicação:
2007
Tipo de documento:
Article