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Syntheses and fluorescent properties of 2-amino substituted 6,7-dimethoxy-4-(trifluoromethyl)quinolines

✍ Scribed by Wolfgang Stadlbauer; Appasaheb B. Avhale; Naresh S. Badgujar; Georg Uray


Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
151 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

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2‐Amino‐substituted 6,7‐dimethoxy‐4‐trifluoromethyl‐quinolines were synthesized from the 2‐oxo compound 1 via 2‐chloroquinoline 2 and aminated with anilines or benzylamine to give highly fluorescent molecules 4, 5. 2‐Aminoquinoline 8 was obtained via azidation of 2, 3, 3a, 3b, 3c, 4, 4a, 4b, 4c, 5, 6A, 6T, reaction to the phosphazene 7, and hydrolysis. 4‐Ethoxycarbonyl derivative 4b is suitable for linking appropriate biomolecules. The construction of a linking group was achieved by conversion of 4b via carboxylic acid 9 to the reactive O‐succinimide ester 10, which reacts easily with amino acids or peptides to amides 11 and 12. The fluorescent properties were investigated and are comparable with derivatives of 1. J. Heterocyclic Chem., (2009).


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