Synthesis, chemical reactivity and biological evaluation of the novel 2-[(1-chloro-3-oxoprop-1- en-1-yl)amino]-4-(4-methoxyphenyl)-6-oxo-1,6- dihydropyrimidine-5-carbonitrile

Abstract

Acetylation of 2-amino-4-(4-methoxyphenyl)-6-oxo-1,6-dihydropyrimidine- 5-carbonitrile (2) using acetic anhydride afforded N-pyrimidinylacetamide derivative 3 which upon formylation using Vilsmeier- Haack reagent produced b-chloroenaldehyde derivative 4. The chemical behavior of compound 4 was investigated toward some primary amines as well as heterocyclic amines yielding the corresponding Schiff bases. Compound 4 is used as a building block for the construction of nitrogen heterocyclic compounds such as pyrazoles, pyrimidines, pyridopyrimidine and diazepine through its reaction with a diversity of bifunctional nucleophiles such as hydrazines, guanidines, 6-aminouracil and ethylenediamine. The biological activity of the synthesized compounds was investigated. Structures of the newly synthesized products were deduced on the basis of their analytical and spectral data.