Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones.

ABSTRACT: Efficient and stereoselective syntheses are described for the preparation of 2,3,9,10-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydroanthracenes 7, 8 and the corresponding 1,4-diol 17 by silver ion-assisted solvolysis of hexabromotetrahydroanthracene 6. Base-promoted aromatization of 7 and 8 afforded synthetically valuable tribromo-1-methoxyanthracenes 10 and 11. The reaction of 17 with sodium methoxide generated tribromodihydroanthracene-1,4-diol 27, whose oxidation with PCC gave 2,9,10-tribromoanthracene-1,4-dione (28). Therefore a selective and efficient method was developed for the preparation of compound 28 starting from 9,10-dibromoanthracene (1), in a simple four-step process. Compounds 10 and 11, and diol 27 constitute key precursors for the preparation of functionalized substituted an

SUBMITTER: Berkil Akar K 

PROVIDER: S-EPMC3167179 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature