Add time:09/06/2019 Source:sciencedirect.com
The condensation of 5-bromoisatin (1a) with aryl methyl ketones (2a–2d) gave 2-aryl-6-bromoquinolines (3a–3d), ammonolysis of which gave the 6-amino-2-arylquinoline derivatives (4a–4d), which were also converted to the corresponding acetyl derivatives 5a–5d by reaction with acetic anhydride. Diazotisation of 4a–4d and coupling with Tobias acid (6) gave o-aminoazo dyes (7a–7d), which were then oxidatively cyclised to the 2-aryl-6-triazoloquinoline derivatives (8a–8d). Treatment of 2-phenyl-6-bromoquinoline-4-carboxylic acid (3a) with cuprous cyanide and copper in quinoline gave 2-phenyl-6-cyanoquinoline (9) which on condensation with 2-aminophenol (10) and 1,2-diaminobenzene (11) yielded 2-phenyl-6-(benzoxazol-2-yl)- and 2-phenyl-6-(benzimidazol-2-yl)-quinolines (12a and 12b, respectively). The possible use of compounds 5a–5d, 8a–8d, 9 and 12a–12b as fluorescent brightening agents was studied.
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