Synthesis and Characterization of New Compounds Containing Heterocyclic Rings Derived From Trimethoprim and Cyclic Anhydrides

Abstract

The present work involves synthesis of new heterocyclic compounds containing multifunctional groups through different strategies. The work was divided into five steps: First step, synthesis of amic acids derivatives (A1-A5) by direct reaction of cyclic anhydrides (phthalic anhydride, nitrophthalic anhydride, succinic anhydride, malic anhydride and itaconic anhydride) with trimethoprim in aceton. Second step, Synthesis of substituted imides (B1-B5) via dehydration of the synthesized amic acid using acetic anhydride and anhydrous sodium acetate as dehydrating agent. Third step involved Synthesis of chloroactyl amides (C1-C5) by reaction of compounds (B1-B5) with chloroacetyl chloride in presence of triethyl amine. Four step include Synthesis of aminothiazole compounds (D1-D5) through cyclization of compounds (C1-C5) by using thiourea in DMF. Five step synthesis of imines compounds (F1-F33) by reaction of amino thiazole compounds (D1-D5) with some aromatic aldehydes and ketones in presence of ethanol solvent. The following scheme summarizes the synthesis sequence for all compounds .