Ullmann reactions of 1-amino-4-bromoanthraquinones bearing various 2-substituents furnishing novel dyes

Enas M. Malik, Mahmoud Rashed, Lukas Wingen, Younis Baqi, Christa E. Müller

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Novel 1-amino-4-(ar)alkylaminoanthraquinone derivatives bearing different substituents (Br, CH2OH, CN, or CH3) at the 2-position of the anthraquinone scaffold were synthesized by copper-catalyzed Ullmann condensation. The 2-substituted 1-amino-4-bromoanthraquinone derivatives (bromaminic acid analogues) were reacted with a variety of alkyl-, aryl-, and aralkylamines. Different reaction conditions were applied depending on the physical state of the amine and the nature of the substituent at the 2-position of the anthraquinone scaffold. A solvent-free synthetic procedure was developed for reactions with liquid amines. Condensation with solid amines required the addition of a solvent, and reaction conditions had to be optimized for each of the anthraquinone derivatives. Our results emphasize that copper-catalyzed reactions are highly variable depending on the molecules and anions present in the medium, since different reaction mechanisms apply. The synthesized anthraquinone derivatives may be useful as new dyes, or may show biological activity and could be employed as tool compounds in experimental pharmacology.

Original languageEnglish
Pages (from-to)33-40
Number of pages8
JournalDyes and Pigments
Volume131
DOIs
Publication statusPublished - Aug 1 2016

Fingerprint

Bearings (structural)
Anthraquinones
Coloring Agents
Dyes
Derivatives
Amines
Scaffolds
Copper
Condensation
Bioactivity
Anions
Negative ions
Molecules
Acids
Liquids

Keywords

  • Anthraquinones
  • Bromaminic acid
  • Dyes
  • Reactive Blue 2
  • Synthesis
  • Ullmann condensation reaction

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

Ullmann reactions of 1-amino-4-bromoanthraquinones bearing various 2-substituents furnishing novel dyes. / Malik, Enas M.; Rashed, Mahmoud; Wingen, Lukas; Baqi, Younis; Müller, Christa E.

In: Dyes and Pigments, Vol. 131, 01.08.2016, p. 33-40.

Research output: Contribution to journalArticle

Malik, Enas M. ; Rashed, Mahmoud ; Wingen, Lukas ; Baqi, Younis ; Müller, Christa E. / Ullmann reactions of 1-amino-4-bromoanthraquinones bearing various 2-substituents furnishing novel dyes. In: Dyes and Pigments. 2016 ; Vol. 131. pp. 33-40.
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