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

Abstract

Abstract magnified image 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).