Synthesis and Characterization of Several New Succinimides Linked to Phenyl Azo Benzothiazole or Thiazole Moieties with Expected Biological Activity

Abstract

In the present work, several new cyclic imides (succinimides) linked to benzothiazole or thiazole moieties through phenyl azo group were synthesized. Synthesis of the new imides was performed via multistep synthesis. The first step involved reaction of equimolar amounts of succinic anhydride and p-toluidine producing N-(4-tolyl) succinamic acid (1) which was dehydrated in the second step via treatment with acetic anhydride and anhydrous sodium acetate affording N-(4-tolyl)succinimide (2).
In the third step, substituted-2-aminobenzothiazoles were introduced in diazotization reaction with nitrous acid producing the corresponding diazonium salts and these inturn were introduced directly in coupling reaction with compound (2) affording the target cyclic imides (3-7). Structures of the new compounds were confirmed by depending on FTIR spectral data and (1HNMR and13CNMR) spectra for some of them which were in good agreement with the proposed ones.