Synthesis of Fluorinated Nitrogen Heterocycles as New Drug Scaffolds

Document Type : Original Article

Author

Master of Science in Pharmacutical Science and Medicinal Chemistry, Loughborough, Loughborough University, UK. Chemistry lecturer, college of health sciences and nursing, Alrayan Colleges, Madinah, Saudi Arabia.

Abstract

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. 

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