Studies on the Condensation of 1,3-Diaryl-propen-1-one with Ethyl Cyanoacetate

Abstract

Michael condensation of 1[p-bromopheny1]-34p-chlorophenyli-propen¬1-one [I] with ethyl cyanoacetate in the presence of ammonium acetate leads to the formation of (II) 6[p-bromopheny1]-2-hydroxy-44p-chlorophenyll nico¬tinonitrile, 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 1H-pyrazolopyridine (XI) and isoxazolopyri¬dine (XII). Also, reaction of (VI) with hydrazine hydrate and (I) with urea, thiourea, hydrazine hydrate, phenylhydrazine and oxidation with hydrogen peroxide are described.