الفهرس 
Title : Utility of Dihydroisoquinoline Derivatives in Synthesis of Some new Heterocyclic Compounds With Expected Biological Activity
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Abstract
The present dissertation describes the utility of isoquinoline derivatives in the synthesis of new heterocyclic compounds for example: pyrazolines, thiazoles, thiadiazoles, pyrroles and pyridines. Stirring of triazoloisoquinolines 13A,B with 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehyde derivatives 14a-e in ethanol in the presence of sodium hydroxide solution to afford chalcones 15A-B. Also, coupling reaction of 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile 2 with diazotized arylamines 19a-s or heterocyclic amines 19t-x in ethanol in the presence of sodium acetate gave 2-(aryldiazenyl)-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidene)acetonitriles 20a-x. Treatment of aldehyde derivative 23 with methyl hydrazinecarbodithioate 24 in refluxing ethanol in the presence of hydrochloric acid gave methyl 2-(2-cyano-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidene)ethylidene)-hydrazine-1-carbodithioate 25, which was converted to thiadiazoles 26-29 and 30-33 by stirring with hydrazonoyl halides 3-6 and 8-11, respectively, in absolute ethanol in the presence of triethylamine. Refluxing of enaminonitrile 22 with thiadiazole derivatives 34 in absolute ethanol in the presence of hydrochloric acid gave 30-33. Thioamide 39 was obtained via refluxing of aldehyde derivative 22 with thiosemicarbazide 38 in absolute ethanol in the presence of acetic acid. Also, refluxing of thioamide 39 with α-ketohydrazonoyl halides 3,5-7 in ethanol in the presence of triethylamine gave thiazoles 40-43. Knoevenagel condensation of compound 2 with 3,4,5-trimethoxybenzaldehyde 45 in absolute ethanol in the presence of hydrochloric acid afforded arylidene 46, which was converted to acetylpyrroloisoquinoline derivative 49 upon refluxing with N-phenyl-C-acetylmethanohydrazonoyl chloride 3C in chloroform in the presence of triethylamine. Claisen–Schmidt condensation of compound 49 with arylaldehydes 50a-c in ethanol in the presence of sodium hydroxide solution gave the corresponding chalcones 51a-c. The latter compounds 51a-c reacted with hydrazine hydrate in refluxing ethanol to afford pyrazoline derivatives 52a-c, which were converted to acetylpyrazolines 53a-c upon boiling in acetic acid. Heating of chalcone 51a with hydrazonoyl chlorides 11A-D in absolute ethanol in the presence of triethylamine at reflux yielded the corresponding pyrazoline cycloadducts 54A-D. Refluxing of acetylpyrroloisoquinoline derivative 49 with methyl hydrazinecarbodithioate 24 in absolute ethanol in the presence of few drops of hydrochloric acid afforded methyl 2-(1-(1-cyano-8,9-dimethoxy-2-(3,4,5-trimethoxyphenyl)-5,6-dihydropyrrolo[2,1-a]isoquinolin-3-yl)ethylidene)-hydrazine-1-carbodithioate 56. Heating of compound 56 with hydrazonoyl halides 3-6,8,11 in refluxing acetonitrile in the presence of triethylamine afforded the corresponding 1,3,4-thiadiazole derivatives 57-62. Also, studying of Hantzsch-like reaction of compound 2 with β-ketoesters 65, 69 and 70 in refluxing acetonitrile in the presence of piperidine afforded 4H-pyrido[2,1-a]isoquinoline 68,72 and 73, respectively. Michael addition reaction of ethyl 3-aryl-2-cyanoacrylates 74a-g with compound 2 in refluxing acetonitrile in the presence of piperidine to yield 4H-pyrido[2,1-a]isoquinoline derivatives 75a-g. The structures of the newly prepared heterocyclic compounds were established on the basis of elemental analyses and spectral data (IR, 1H NMR, 13C NMR and MS). Also, some of the new compounds were tested for their anticancer, antibacterial and antifungal activities.