(Tosyloxy)anthraquinones: Versatile Synthons for the Preparation of Various Aminoanthraquinones

Article abstract of DOI:10.1021/jo00383a025

Various aminoathraquinones can be easily prepared from (tosyloxy)anthraquinone precursors.Unsymmetrical 1,4-diaminoanthraquinones are prepared via the intermediate monoamino mono(tosyloxy)anthraquinones derived from 1,4-bis(tosyloxy)anthraquinone.The ability to remove tosylate groups sequentially is controlled by the proper selection of solvent and temperature.Hindered 1,4-diamino and 1-aminoanthraquinones are prepared from their corresponding tosyl derivatives, and the amount of steric hindrance present can be succesfully correlated with spectral and color data.The methods described offer advantages over the literature preparations of these compounds.