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

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,...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2009-05, Vol.46 (3), p.415-420
Main Authors: Stadlbauer, Wolfgang, Avhale, Appasaheb B., Badgujar, Naresh S., Uray, Georg
Format: Article
Language:English
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Summary: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).
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.109