Thesis (M.Sc.) - Cairo University - Faculty of Science - Department of Organic Chemistry

The present dissertation describes the utility of isoquinoline derivatives in the synthesis of new heterocyclic compounds by treatment of 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1- yl)acetonitrile 1 with arylisothiocycnates 2a-c in refluxing toluene to afford thioanilide derivatives 3, which converted to the corresponding thiadiazole derivatives 5A-P upon refluxing with Ü-ketohydrazonoyl halides 4A-P in chloroform in the presence of triethylamine. Refluxing of thiadiazoles 5A-C with N,N-dimethylformamide dimethylacetal afforded enaminones 11A-C. Also, study the Michael addition reaction of enaminones 14a-d with compound 1 in refluxing ethanol in the presence of piperidine to yield 4H-pyrido[2,1-a]isoquinoline-1-carbonitrile derivatives 16a-d. Also, reaction of and ethyl 3-aryl-2-cyanoacrylate 19a-g with compound 1 under the same previous conditions, using acetonitrile instead of ethanol, gave 4H-pyrido[2,1- a]isoquinoline-1,3-dicarbonitrile derivatives 23a-g. Stirring of aldehydes 24a-i with 1 in absolute ethanol in the presence of concentrated hydrochloric acid gave the corresponding arylidene derivatives 25, which converted to 5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carbonitrile derivatives 28a-g by refluxing with Ü-ketohydrazonoyl halides 4A,G,K in chloroform in the presence of triethylamine. The structures of the new heterocyclic compounds prepared were established on the basis of elemental analysis and spectral analyses (IR, ¹H NMR, ¹³C NMR, MS). Also, some of the new compounds were tested for their antibacterial and antifungal activities

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