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Abstract
The present dissertation describes the utility of hydrazonoyl halides in the synthesis of some new heterocyclic compounds. Reaction of such halides with 4,4-dimethyl-2,6-dioxocyclohexane-thiocarboxamides led to the formation of the corresponding thiadiazoles. Also, their reaction with enaminone derived from 2-[5-acetyl-3- phenyl-1,3,4-thiadiazol-2(3H)-ylidene]-5,5-dimethylcyclohexane-1,3-dione yielded the corresponding 2-(1-aryl-3- substituted-pyrazol-4-carbonyl)-5-[3-phenyl-5-(5,5-dimethylcyclohexane-1,3-dione)-[1,3,4]-thiadiazole] derivatives. In addition, the thesis presents a novel method for synthesis and reaction of bis-1,3-dipole e.g. N,N’-biphenyl-1,3- benzene-bis-carbohydrazonoyl bromide 8. Reactions of bis-hydrazonoyl bromide 8 with each of KSCN and KSeCN yielded the corresponding bis-thiadiazoline 9A and bis-selenadiazoline 9B. Bis-pyrazole derivatives 14a-c and 15ab were also obtained by reactions of 8 with the appropriate active methylene compounds. Reactions of 8 with each of 1,2-dicyanoethylene, acenaphthylene and phenyl-5-arylidene-2-thioxo-thiazol-4-one as dipolarophiles yielded the corresponding cycloadducts 16, 19 and 20, respectively