Synthesis of 2,4-disubstituted thiazoles from (Z)-(2-acetoxyvinyl)phenyl-lambda3-iodanes: nucleophilic substitution of alpha-lambda3-iodanyl ketones with thioureas and thioamides.
In the presence of triethylamine, (Z)-(2-acetoxy-1-alkenyl)phenyl-lambda(3)-iodanes react with thioureas or thioamides in MeOH to give 2,4-disubstituted thiazoles directly in good yields. The reaction probably involves generation of highly reactive alpha-lambda(3)-iodanyl ketones through ester exchange of the beta-acetoxy group with liberation of methyl acetate, followed by nucleophilic substitutions with thioureas or thioamides.