Synthesis of some new N-saccharin derivatives of possible biological activity.

Ahmed Wahed Naser and Aseel Fa

Abstract

In the present work a variety of new heterocyclic compounds namely thiazole ,oxazole , oxazoline, cyclicimide, Blactam and oxazpeine were synthesized using α-(N-saccharin) acetate (1) as a starting material .A series of Schiff bases (3-5) have been synthesized by condensation of α- (N-saccharin)acetohydrazide (2) with various aromatic aldehydes namely p-bromobenzaldehyde, p-chlorobenzaldehyde and p-methoxybenzaldehyde. Cyclization of (3-5) with maleic anhydride, succinic anhydride, phthalic anhydride and chloroacetylchloride gave the corresponding oxazpeine (6-14) and azitidine (15-17) derivatives. Reaction (1) with urea and thiourea gave carbonyl derivative (18) and carbonthioyl derivative (19).Compounds (18, 19) that cyclized either with p-bromophenacyl bromide and p-phenylphenacyl bromide to give the corresponding 1, 3-oxazole (20, 21) and 1, 3 thiazole (22, 23) derivatives. The carboxamide derivatives (24, 25) were obtained by condensation of (2) with phenylisocynate and 1- naphtylisocynate. Compounds (24, 25) that cyclized either p-bromophenacyl bromide or p-phenylphenacyl bromide to give the corresponding oxazoline derivatives (26-29). Reaction (2) with various acid anhydrides namely maleic anhydride, succinic anhydride and phthalic anhydride in presence acetic acid gave the corresponding cyclicimide derivatives (30-32). F.T.IR and 1- HNMR were used to characterize the target compounds.