Synthesis and Characterization of Some New Dioxoisoindolin Compounds Containing Thiazine, Azetidine, Thiazolidine and Amide Moities

Abstract

A compound (1) was done through thiosemicarbazide cyclization in presence of (CS2) and anhydrous of (Na2CO3) in ethylalcohol. Compound (1) was treated with substituted aromatic aldehydes to produced 2- [(subrogateed benzyliden) amino] 1,3,4-thiadiazole (2). Schiff bases prepared by reaction of 2-carboxy thiophenol with (Et3N) to give compound (4). Then the compound (4) was interact with chloro acetyl chloride in Et3N to collect the compound (3). Compound (5) 4- (1,3-dioxoisoindolin-2-yl) benzoic acid was prepared from reaction between p-amino benzoic acid and phthalic anhydride in acetic acid and then converted into the 4 - (1,3-dioxoisoindolin-2-yl) benzoyl chloride (6) by use thionyl chloride. The reaction of acyl chloride with appropriate primary amine gives amide derivatives (14a-i) while the reaction of acyl compound (6) with thiol derivatives gave compounds (7,8 and 9). Compound (12) was synthesized by the reaction of compound (6) with hydrazine hydrate. Then reacted with appropriate benzaldehyde to give compound (13). The reaction between 4- (1,3-dioxoisoindolin-2-yl) benzoic acid (5) and one mole of thiosemicarbazide in presence of phosphorousoxychloride give compound (10) which reacted with p-nitrobenzaldehyde to afford compound (11).