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Abstract This work has been carried out to investigate the chemical reactivity and synthetic potentiality of 2-thioxodihydrohydropyridine 6a,b via their reaction with several active halogen-containing compounds to afford the corresponding 2-alkylthiopyridine in some cases and thieno[2,3-b]pyridine directly in most cases. Thieno[2,3-b]pyridine-2- carbohydrazides 10a,b obtained through the reaction of 2- methoxycarbonylthienopyridines 9a,j with hydrazine hydrate which in turn, used to obtain the corresponding pyrimidinones 16a,b, 18a,b, pyrazolothienopyridine derivatives and 1,3,4-oxdiazoles. 3-Aminopyrazolopyridines 35a,b obtained via the reaction of 6a,b with hydrazine hydrate which in turn, reacted with nitrous acid to give the diazonium salts 36a,b which coupled with several active-hydrogen containing reagents to give the corresponding triazines. Bis compounds have received great attention, thus Bis[2-thioxo-1,2-dihydropyridine-3-carbonitrile] derivatives 90a,b have been prepared and used as good synthons for the preparation of several bis S- alkyl derivatives 91a-d,g-j[e,f] which cyclized afford bis(3-aminothieno[2,3- b]pyridine) derivatives 92a-j. The structures of all newly synthesized heterocyclic compounds were elucidated by considering the data of IR, 1H NMR (eppm), mass spectra as well as that of elemental analyses |