24094-46-0Relevant academic research and scientific papers
Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs
Malik, Enas M.,Baqi, Younis,Müller, Christa E.
supporting information, p. 2326 - 2333 (2016/02/12)
Anthraquinone (AQ) derivatives play a prominent role in medicine and also in textile industry. Bromaminic acid (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 bromaminic acid 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 bromaminic acid derivatives in excellent isolated yields (>90%) and high purities. Alternatively, 1-amino-4-bromo-2-hydroxymethylanthraquinone could be directly converted to the desired 2-substituted bromaminic acid analogues in high yields (85-100%). We additionally report the preparation of bromaminic acid sodium salt and 1-amino-2,4-dibromoanthraquinone directly from 1-aminoanthraquinone in excellent yields (94-100%) and high purities. The synthesized brominated AQs are valuable precursors for the preparation of AQ drugs and dyes.
Synthesis of Some Disperse Anthraquinone Dyes
Metwally, Saoud A. M.,Youssef, Mohamed S. K.,Younes, Mansour I.
, p. 3007 - 3011 (2007/10/02)
1-Hydroxy- and and/or 1-aminoanthraquinones was allowed to react with formaldehyde in an alkaline medium to give 1-hydroxy- or 1-amino-2-hydroxymethyl-9,10-anthracenediols, which gave by air oxidation, (hydroxymethyl) anthraquinone derivatives.Interaction
