Abstract

SYNTHESIS OF NEW HETEROCYCLIC COMPOUNDS DERIVED FROM 3-CHLOROBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE

Abdul Jabar Kh. Atia., *Mohammed F. Al-Marjani and Muayad A. Qaban

Abstract

In this work twenty-three compounds derived from cinnamic acid were synthesized. Acid chloride(C1) was synthesized by the reaction of cinnamic acid and thionyl chloride . Carbohydrazide (C2) was obtained by the reaction of 3-Chlorobenzo[b]thiophene-2-carbonyl chloride (C1)with hydrazine hydrate. Compound(C2) undergoes the character condensation reaction with different aromatic aldehyde in absolute ethanol gave the Schiff′s bases (C3-C6) . Treating a phenylacetic acid in triethylamine with Schiff′s bases (C3-C6) in the presence of SOCl2 to form the appropriate β-lactams (C8-C10). Reaction of compound (C1) with glycine in sodium hydroxide solution gave acid (C11). Oxazole derivatives was synthesized by the reaction of (C11) with different aromatic aldehyde in acetic acid and acetic anhydride gave (C12,C13). Imidazole derivatives was synthesized by the reaction of hydrazine hydrate in dry benzene with different oxazole derivatives to give (C14,C15).Compounds (C14,C15) undergoes the character condensation reaction with different aromatic aldehyde in absolute ethanol gave Schiff′s bases (C16-C19) . Reaction of imine derivatives (C16-C19) with phenylacetic acid in the presence of SOCl2 to form the anther appropriate β-lactams (C20-C23 ) . The product compounds was characterized by FTIR , U.V and 1HNMR spectrum.

Keywords: cinnamic acid, ?-lactams, oxazole, Imidazole