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 β-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.

摘要

2-氨基-4-(4-甲氧基苯基)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile ( 2 ) 使用乙酸酐乙酰化得到N-嘧啶基乙酰胺衍生物3，使用 Vilsmeier-Haack 试剂甲酰化产生 β-氯烯醛衍生物4．研究了化合物4对一些伯胺以及产生相应席夫碱的杂环胺的化学行为。化合物4通过与多种双功能亲核试剂（如肼、胍、6-氨基尿嘧啶和乙二胺）反应，用作构建含氮杂环化合物（如吡唑、嘧啶、吡啶并嘧啶和二氮杂）的结构单元。研究了合成化合物的生物活性。新合成产物的结构是根据它们的分析和光谱数据推导出来的。