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

The present dissertation includes the results of the synthesis of new heterocyclic compounds using N,2-diaryldiazene-1-carbohydrazonoyl chlorides and other hydrazonoyl halides. The first part of the thesis concerned with using of N,2-diaryldiazene-1-carbohydrazonoyl chlorides in synthesis of novel 5-phenyldiazenyl-1,3,4-thiadiazole derivatives, 3-phenyldiazenyl spiro heterocycles and 3-phenyldiazenyl-1H-pyrazole derivatives. For this purpose reaction of 2- ((methylthio)carbonthioyl)hydrazones 7 with N,2-diaryldiazene-1-carbohydrazonoyl chlorides 1,2 at room temperature in absolute ethanol in the presence of triethylamine afforded the corresponding 1,3,4-thiadiazoles 11,12 (Scheme 1). Also, the latter products 11,12 were prepared by treatment of 2-hydrazono-3-aryl-5-(aryldiazenyl)-2,3-dihydro-1,3,4-thiadiazoles 9,10 with the appropriate aldehydes and ketones in 2-propanol in the presence of few drops of hydrochloric acid at reflux. The latter products 9,10 were prepared via stirring of methyl hydrazinecarbodithioate 6 with N,2-diaryldiazene-1-carbohydrazonoyl chlorides 1,2 at room temperature in absolute ethanol in the presence of triethylamine (Scheme 1)

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