Abstract

A CONVENIENT SYNTHESIS OF ETHOXYPHTHALIMIDE DERIVATIZED QUINAZOLINE ASSEMBLED PYRIMIDINE AND PYRIDINE VIA COMMON INTERMEDIATE CHALCONE AND THEIR ANTIMICROBIAL AGENTS

R. R. Dangi*, N.S. Chundawat and G L Talesara

Abstract

In the present investigation, synthesis of 3-{4-[2-amino-6-(4- chlorophenyl)-1,6-dihydropyrimidin-4-yl]phenyl}-1 Nethoxyphthalimido quinazoline-2,4-dione 5a-d and 2-amino-6-(4- chlorophenyl)-4-[4-(2,4-dioxo-1,4-dihydroquinazolin-3-yl)phenyl] }-1- Nethoxyphthalimido pyridine-3-carbonitrile 6a-d is described. Nucleophilic aza substitution on isatoic anhydride with paminoacetophenone gave 3-(4-acetylphenyl) quinazoline-2, 4-dione (1). This on Claisen condensation with various aromatic aldehydes 2ad yields the corresponding 3-{4-[3-(4-substitutedphenyl) prop-2-enoyl] phenyl}quinazoline-2,4-dione 3a-d derivateives.This was condensed by bromoethoxyphthalimide to afford - [4-{3-(4- subsitutedphenyl)prop-2-enoyl}phenyl]-1-Nethoxyphthalimidoquinazoline- 2,4-dione 4a-d. These compounds 4a-d were cyclized separately with guanidine nitrate and malononitrile in ammonium acetate to give two series of final compound 5a-d and 6a-d. Structures of synthesized compounds have been assigned on the basis of their analytical and spectral data. Antibacterial and antifungal activities of the final compounds have been evaluated. Some of the compounds have shown significant inhibition on bacterial and fungal growth.

Keywords: Isatoic anhydride, pyrimidine, pyridine, Bromoethoxyphthalimide, Antimicrobial activity.