Synthesis and Characterization of New Saccharin Derivatives

Abstract

This work involves the synthesis of novel saccharin derivatives. Compound (1) was synthesized via the reaction of saccharin with ethylenediamine in the presence of a few drops of glacial acetic acid. The reaction of compound (1) with phenyl isothiocyanate yielded compound (2). Acetylation of compound (1) produced compound (3). Pyrazole and pyranopyrazole derivatives (5 and 6) were prepared from the saccharin hydrazide compound (4). Additionally, a series of N-alkyl saccharin derivatives (7–14), along with compounds (17 and 18), were obtained by reacting sodium saccharin with appropriate halo compounds, as illustrated in Schemes 2 and 3. Condensation of compounds (7 and 11) with ethylenediamine in the presence of a few drops of glacial acetic acid afforded compounds (15 and 16). Hydrolysis of compounds (17 and 18) in acetic acid medium gave compounds (19 and 20). Compound (21) was synthesized by reacting compound (17) with hydrazine. Finally, compound (22) was obtained from the reaction of compound (21) with p-chlorobenzaldehyde.