Approaches to Iodinated Derivatives of Vanillin and Isovanillin

摘要

The chemistry of vanillin (1) and isovanillin (2) has been examined and reviewed extensively. A current project in our laboratory required the conversion of 5-iodoisovanillin ethers 6a-d to substituted 2,4-diaminopyrimidines followed by Heck coupling with an unsaturated ketone to generate agents displaying inhibitory activity against Bacillus anthracis, a potential bioterror threat.4 The chemistry to prepare 5-iodovanillin ethers 6a-d with variation at C-4 is straightforward starting from commercial 5-iodovanillin (3).