Dichlofenac (2-[(2,6-Dichloroanilino)Phenyl]Acetic Acid) As A Precursor To New Heterocyclic Compounds

Abstract

Anew series of five and six membered ring heterocyclic compounds weresynthesized using 2-[(2,6-dichloroanilino) phenyl] acetic acid (Dichlofenac)(1) as starting material. This compound was converted to its ethyl esterderivative (2) via the acid catalyzed esterification. The ester (2) wasconverted to the hydrazide derivative (3) through its reaction with hydrazinehydrate. The hydrazide (3) was used as precursor to synthesize the heterocyclecontaining compounds. Moreover, the hydrazide (3) was converted to thethiosemicarbazide derivatives (5-7) by their reaction with isothiacyanatecompounds. The compounds (5-7) were converted to five membered ringheterocyclic compounds, such as, 1,3,4-triazols (8, 9, 12, 13),1,3,4-thiadiazoles (10, 11) and 1,3,4-oxadiazol (14) under the influence of amiscellaneous of reagents. The cabohydrazide (3) was incorporated in to1,3,4-oxadiazol (4), phthalimido derivative (15), tetrazinecompound (17), pyrazolines (18-22) and isocyanate compound (24). All thesynthesized compounds were characterized by physical and spectral data.