Synthesis of 2-aroylisoindoline-1, 3- dione from phthalimide

Abstract

Phthalimide(Isoindoline-1, 3-dione) derivatives have received attention due to their antibacterial, antifungal, analgesic, antitumour, anxiolytic and anti HIV-1 activities. Isoindoline 1,3-dione derivatives can be used as promising and effective drugs for the treatment of different diseases such as AIDS, tumour, diabetes, multiple myeloma, convulsion, inflammation, pain, bacterial infection. A convenient, general and facile method for the synthesis of aroylsubstituted isoindoline-1, 3- dione(7-11) from Phthalimide has been developed. The reactions of Phthalimide (1) with aroylchlorides (2-6)were performed in the presence of Lewis acid (AlCl3) and also in absence of acid in different solvents under mild conditions in good yield %. Scheme-1:  2, 7 R= C6H4CH3 (p)  3, 8 R= C6H4Cl (p)  4, 9 R= C6H5  5, 10 R= CH3 1 2-5 7-10 Scheme-2:  6, 11 R= SO2C6H4CH3 (p) All the synthesized compounds were characterized by IR, 1H-NMR and 13C-NMR spectra and Elemental Analysis to establish the structure.