Synthesis of some heterocyclic compounds derived from 1-Aryl-3-(4-hydroxy-3-methoxyphenyl) propene-1-one

Abstract

A series of heterocyclic compounds have been synthesized using 1–aryl-3-(4-hydroxy-3-methoxypheny) prop-2-ene-1-one (1-4) as starting material which was prepared by claisen-schmidt condensation between vanillin and substituted acetophenone.Benzoxazepine derivatives (5-8) and benzodiazepine derivatives (9-12) were synthesized from the reaction of o-aminophenol, o-phenlendiamine with compounds (1-4) respectively. Thereaction of compounds (1-4) with hydrazine hydrate afforded pyrazol derivatives (13-16). While the reaction of compounds (1-4) with hydrazine hydrates in the presences a few drops of glacial acetic acid gave 1- acetyl pyazol derivatives (17-20). Oxirane derivatives (21-24) were synthesized from the reaction of compounds (1-4) with hydrogen peroxide in the basic medium. Reaction of phenylthiourea with compounds (1-4) afforded pyrimidinethion derivative (25-27).Finally isoxazol derivatives (28-31) were synthesized by the reaction of compounds (1-4) with hydroxylamine hydrochloride in presences of triethylamine.