Synthesis and characterization of novel schiff bases of imide moiety

Abstract EN

In our research novel schiff bases of imides moiety have been synthesized.

Novel Schiff base derivatives of imides moiety have been synthesized by multistep reaction.

First step involves prepare 2-amino -5-mercapto-1,3,4-thiadiazole (I) by the cyclization of thiosemicarbazide with carbon disulphide and anhydrous sodium carbonate in ethanol as a solvent.

Then, compound (I) was reacted with phthalic anhydride in the presence of glacial acetic acid to give 2-(5-mercapto-1,3,4-thiadiazol-2-yl) isoindoline-1,3-dion (II).

Compoun (II) was heated with ethyl chloracetate in the presence of potassium carbonatproduced ethyl 2- (5-(1,3-dioxoisoindoline -2-yl)-1,3,4-thiadiazole-2-yl thio) acetate (III).

The reaction of compound (III) with hydrazine hydrate yielded 2-(5-(1,3-dioxoisoindoline -2-yl)-1,3,4- thiadiazol-jm2-ylthio) acetohydrazide (IV).

The fifth step involves reaction of compound (IV) with N,N-dimethyl aminobenzaldehyde to yield N´-(4-(dimethyl amino)benzylidene )-2-(5- (1,3-dioxoisoindoline-2-yl)-1,3,4-thiadiazole-2-yl-thio)acetohydrazide (V).The structures of the newly synthesized compounds were confirmed by physical properties and spectral (FTIR, 1H-NMR) analysis.