Synthesis of Fluorinated Nitrogen Heterocycles as New Drug Scaffolds
Amani Hasan Hasoubah ,
The amine compound (N-(2-bromophenyl)-4-methyl-N-(perfluoropyridin-4-yl)benzenesulfonamide) was successfully synthesised which was needed to find a strategy to synthesise fluorinated nitrogen heterocycles. The aim of this study was to make a cyclised product by treating the amine compound with different reagents to effect metalation in the bromophenyl group which could result in SNAr reaction in the fluorinated ring. However, treating the target compound with Bu-Li or Mg interestingly gave two different compounds which had lost the sulfonyl group. In addition, the reaction of (N-(2-bromophenyl)-4-methyl-N-(perfluoropyridin-4-yl)benzenesulfonamide) with Cu and 2-bromophenyltetrafluoropyridinamine with Cu was unsuccessful due to the recovery of the starting material as a major product and a minor percentage of new compounds had formed.