Utility of Oxo-Compounds as Synthons of Some Heterocycles

Abstract

Part I: N'-((2-chloroquinolin-3-yl) methylene) 2-cyanoacetohydrazide (1) which was synthesized from 2-choloroquinolin-3-carbaldehyde was allowed to react with different nucleophilic and electrophilic reagents to construct new heterocycles which might have considerable potency as antimicrobial agents. Thus, compound 1 was boiled with hydrazine hydrate and phenyl hydrazine to afford the pyrazolo derivatives 2 and 3. On the other hand, its treatment with 2-cyanoacetohydrazide, it gave the diazepine derivative 4. On treating compound 1 with isatin in boiling dioxane and few drops of piperidine as a base it yielded the adduct 5. Refluxing of compound 1 with anthranilic acid gave quinoline derivative 6. On the other hand, treatment of compound 1 with salicylaldehyde furnished chromene derivative 7 in a good yield. Heating a mixture of compound 1 and diethyl acetylenedicarboxylate in dioxane with few drops of piperidine afforded the furopyrrolodiazole derivative 8 and the pyrrolo-pyridazine derivative 9.