Abstract
A new series of 5-substituted-cinnamoyl-8-hydroxyquinoline (la-e) were prepared via the reaction of 5-acetyl-8-hydroxyquinoline with the selected aldehydes. 5 Pyrazolino-, isooxazolino-, and/or pyrmidine-thiono-8-hydroxyquinoline (2-4 respectively) were obtained from the reaction of 1a-e with hydrazines, hydroxylamine and thiourea. Michael addition of active methylene compounds, e.g. malononitrile, cyanoethyl acetate, to the chalcones (1a-e) in presence of ammonium acetate gave the corresponding nicotinonitrile derivatives (6 and 7) while the reaction of 1 with ethyl acetoacetate gave the cyclohexenone derivative (8) containing 8-hydroxyquinoline moiety.