
TY  - JOUR
A1  - Mahadevan, IB 
A1  - Kimber, MC 
A1  - Lincoln, SF 
A1  - Tiekink, ERT 
A1  - Ward, AD 
A1  - Betts, WH 
A1  - Forbes, IJ 
A1  - Zalewski, PD 
T1  - The Synthesis of Zinquin Ester and Zinquin Acid, Zinc(II)-Specific Fluorescing Agents for Use in the Study of Biological Zinc(II)
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 5
SP  - 561
EP  - 568
KW  - 
UR  - https://doi.org/10.1071/CH9960561 
N2  - The syntheses of Zinquin ester [ethyl [2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetate] and the corresponding acid, both of which are zinc(II)-specific fluorophores , are described. 6-Methoxy-2-methyl-8-(p- tolylsulfonylamino ) quinoline (2) can be demethylated , with boron tribromide, to form either the expected phenol or a mixture of the phenol and the corresponding 5-bromo derivative depending upon the reaction conditions. These compounds react with ethyl bromoacetate to give the corresponding esters, as well as the 5-ethoxycarbonyl derivative formed by electrophilic substitution. Halogenation of the sulfonamide (2) occurs readily at the 5-position. The 5-iodo product undergoes a Heck coupling with ethyl acrylate . The crystal structures of ethyl [5-ethoxycarbonylmethyl-2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetate and [5-carboxymethyl-2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetic acid are described. 
ER  -

