Synthesis of basic Hansa Yellow analogs and their butylamino derivatives from N-amino-3-acetoacetamidopyridinium 2,4-dinitrophenate

Add time:07/18/2019    Source:sciencedirect.com

In a multi-step synthesis a series of new basic dyes (4a–4g, 5a–5g and 8a–8g) were prepared starting from 3-(acetoacetamido)pyridine. Whilst coupling of arene-diazonium salts with N-amino-3-(acetoacetamido)pyridinium 2,4-dinitrophenate afforded the N-aminopyridinium cationic dyes (4a–4g) which exist in the hydrazone configuration, the introduction of an alkylamino moiety into the latter dyes gave new basic arylazo dyes (5a–5g), in which double intramolecular hydrogen bonding is a principal structural feature. Reaction of these dyes with p-dimethylaminobenzaldehyde yielded a further series of basic dyes (8a–8g). The structure of the dyes was inferred from elemental and spectral analysis and, in some cases, by alternative synthetic routes.

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