Synthesis and Microbial Activity of 5-Heterocyclo-8-hydroxyquinolines

Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt

Manuscript received 24 March 1986, revised 27 March 1990, accepted 22 August 1990

A new series of  5-substituted cinnamoyl-8-hydroxyquinoline (1a-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  la-e with hydrazines, hydroxylamine and thiourea. Michael addition of active methylene compounds, e.g. malononitrile, cyanoethyl acetate, to the chalcones (la -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.