- Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs
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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.
- Malik, Enas M.,Baqi, Younis,Müller, Christa E.
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supporting information
p. 2326 - 2333
(2016/02/12)
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- Synthesis of Some Disperse Anthraquinone Dyes
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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
- Metwally, Saoud A. M.,Youssef, Mohamed S. K.,Younes, Mansour I.
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p. 3007 - 3011
(2007/10/02)
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