Synthesis and characterization of chloromaleimidobenzenesulfonylhydrazones

This paper describes the synthesis of a new series of imidosulfonylhydrazones in a search for antibactericidal and/or antinociceptive lead compounds. Cyclic imides comprise an important family of organic compounds with therapeutic potential, including the sulfonylhydrazones. 3,4-Dichloro-1-phenyl-1H-pyrrole-2,5-dione (1) was obtained from the reaction between aniline and dichloromaleic anhydride in acetic acid. Reaction of (1) with pyrrolidine gave 3-chloro-1-phenyl-4-pyrrolidin-1-yl-1H-pyrrole-2,5-dione (2). 4-(3-Chloro-2,5-dioxo-4-pyrrolidin-1-yl-2,5dihydro-1H-pyrrol-1-yl) benzenesulfonyl chloride (3) was obtained from the chlorosulfonation of compound (2). The reaction of (3) with hydrazine hydrate produced 4-(3-chloro-2,5-dioxo-4-pyrrolidin-1-yl-2,5-dihydro-1H-pyrrol-1-yl) benzenesulfonohydrazide (4), which was characterized through condensation with aldehydes to yield the imidosulfonylhydrazones (5-12).