Synthesis of 2-Aryl-6-substituted quinolines and their use as fluorescent brightening agents |
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| Affiliation: | 1. Faculty of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China;2. School of Material Science and Engineering, Jiangsu University, Zhenjiang 212013, China;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, Cairo, P.O. Box 11562, Egypt;2. Research Unit, Saco Pharm. Co., 6th October City, Egypt;1. College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu South Road, Nanjing 211816, China;2. State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, 30 Puzhu South Road, Nanjing 211816, China;1. State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu Province, 210093, PR China;2. College of Sciences, Nanjing Tech University, Nanjing, Jiangsu Province, 210009, PR China |
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| Abstract: | 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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