Beilstein J. Org. Chem.2015,11, 2326–2333, doi:10.3762/bjoc.11.253
, Postal Code 123, Muscat, Oman 10.3762/bjoc.11.253 Abstract Anthraquinone (AQ) derivatives play a prominent role in medicine and also in textile industry. Bromaminicacid (1-amino-4-bromoanthraquinone-2-sulfonic acid) is an important precursor for obtaining dyes as well as biologically active compounds
through the replacement of the C4-bromo substituent with different (ar)alkylamino residues. Here we report methods for the synthesis of bromaminicacid analogues bearing different substituents at the 2-position of the anthraquinone core. 1-Aminoanthraquinone was converted to its 2-hydroxymethyl
-substituted derivative which, under different reaction conditions, yielded the corresponding carbaldehyde, carboxylic acid, and nitrile derivatives. The latter was further reacted to obtain 1-amino-2-tetrazolylanthraquinone. Subsequent bromination using bromine in DMF led to the corresponding bromaminicacid
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Graphical Abstract
Figure 1:
Structures of the anthraquinone derivatives Reactive Blue 2 (RB-2) and bromaminic acid sodium salt.