Michael condensation of l[p-bromophenyl]-3-[p-chlorophenyl]-propen- I-one [I] with ethyl cyanoacetate in the presence of ammonium acetate leads to the formation of (II) 6-[p-bromophenyl]-2-hydroxy-4-[p-chlorophenyl] nicotinonitrile, and nicotinamide (III) as a major product. The reaction of (II) with phosphorous oxychloride, Grignard reagents and ethyl bromoacetate gives, 2-chloro-(IV), 3-acyl-(X) and 2-alkoxy (VII) pyridine derivatives. Reactions of (IV) with amines, hydrazine hydrate, sodamide and alkoxides are also investigated. (X) reacted with hydrazine hydrate and hydroxylamine hydrochloride to give substituted IH-pyrazolopyridine (XI) and isoxazolopyridine (XI I). Also, reaction of (VI) with hydrazine hydrate and (I) with urea, thiourea, hydrazine hydrate, phenylhydrazine and oxidation with hydrogen peroxide are described.
I ATTIA ,S EL NAGDY ,F A EL BASSIOUNY ,M R MAHMOUD ,
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