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- W2022031210 abstract "The simplest 1-arylazoanthraquinones have been known for a long time [1]. (4-Hydroxyphenylazo)anthraquinones typically give rise to azo3quinonehydrazone tautomerism [2], while the other chemical properties of these compounds were poorly studied. Taking into account high reactivity of various halogen-substituted anthraquinones in nucleophilic amination [3], we have examined the reactions of 4-chloro-1-(4-hydroxyphenylazo)anthraquinone (Ia) and 4-chloro-1-(4-dimethylaminophenylazo)anthraquinone (Ib) with cyclohexylamine, morpholine, and piperidine. Compounds Ia and Ib reacted with highly nucleophilic amines in dimethylformamide at 603 80oC and in dimethylacetamide at 50360oC within several hours (Scheme 1). The reactions with weakly nucleophilic amines required more severe conditions and were not selective. We failed to synthesize 4-amino-1-arylazoanthraquinones by the other method, namely by reaction of diazotized 1-amino-4-RNH-anthraquinones with phenol or dimethylaniline. In all cases, products of other transformations were isolated instead of the expected azo coupling products. For instance, from diazotized 1-amino-4-cyclohexylaminoanthraquinone and phenol in dimethylformamide we obtained 1,1-dimethyl-3-(9,10-dioxoanthracen-1-yl)triazene. When dimethylformamide was replaced by water, the product was 1-cyclohexylaminoanthraquinone. The latter was also obtained by attempted azo coupling of the same diazonium salt with N,N-dimethylaniline in dimethylformamide. The structure of compounds IIa3IIc and III was confirmed by elemental analyses and IR, H NMR, and mass spectra. 1-Cyclohexylamino-4-(4-hydroxyphenylazo)anthraquinone (IIa). A mixture of 1.1 mmol of anthraquinone Ia [4], 11 mmol of cyclohexylamine, and 5 ml of dimethylacetamide was stirred at 50360oC for 4 h (until initial anthraquinone Ia disappeared according to the TLC data). The mixture was cooled to room temperature and diluted with water. The dark brown tar-like precipitate was filtered off, washed with water and aqueous ethanol, dried, and subjected to column chromatography on silica gel (40/100 mm)" @default.
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- W2022031210 date "2010-05-21" @default.
- W2022031210 modified "2023-09-28" @default.
- W2022031210 title "ChemInform Abstract: Amination of 1-Arylazo-4-chloroanthraquinones." @default.
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- W2022031210 doi "https://doi.org/10.1002/chin.200222111" @default.
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