
%0 Journal Article
%A Mahadevan, IB 
%A Kimber, MC 
%A Lincoln, SF 
%A Tiekink, ERT 
%A Ward, AD 
%A Betts, WH 
%A Forbes, IJ 
%A Zalewski, PD 
%T The Synthesis of Zinquin Ester and Zinquin Acid, Zinc(II)-Specific Fluorescing Agents for Use in the Study of Biological Zinc(II)
%J Australian Journal of Chemistry
%D 1996/05/01
%V 49
%N 5
%P 561-568
%K 
%R https://doi.org/10.1071/CH9960561
%U https://www.publish.csiro.au/paper/CH9960561 
%X 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. 
