Synthesis and pharmacological studies on some phthalimidoxy substituted quinoline derivatives

Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, M. L. Sukhadia University,

Udaipur-313 001, Rajasthan, India

E-mail : gtalesara@yahoo.com

Manuscript received 30 September 2008, revised 1 April 2009, accepted 26 June 2009

Synthesis of novel N'-[2-(4-substitutedphenyi)-3-N-ethoxyphthalimido-5-oxoimidazolidene-1-yl]-2-(quinoline-8- yloxy)acetamide derivatives (6a-e) with potential biological activities were carried out by adopting the reaction scheme given below. Compound ethyl-(quinoline-8-yloxy)acetate (2) was synthesized by renuxing 8-hydroxyquinoline with ethylchloroacetate in presence of K₂CO₃ . Ethyl-(quinoline-8-yloxy)acetate (2) was converted to corresponding hydrazide (3) on treatment with hydrazine hydrate which on further condensation with various araldehydes gave respective Schiff's bases (4a-e). These on cyclisation with glycine yielded corresponding oxoimidazolidenes (5a-e). Active H of lmidazolidinones (5a-e) was replaced by ethoxy phthalimide to yield final products (6a-e).