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
Farouk, Osama; Nasser M. El-Gohary; Magdy A. Ibrahim;
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.
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.
Other data
Title | 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 | Authors | Farouk, Osama ; Nasser M. El-Gohary; Magdy A. Ibrahim | Keywords | Antimicrobial evaluation;cyclocondensation;nucleophilic reactions;pyrazoles;pyrimidines;Vilsmeier–Haack | Issue Date | Jul-2021 | Journal | Synthetic Communications | Volume | 51 | Issue | 19 | Start page | 2991 | End page | 3003 | ISSN | 00397911 | DOI | 10.1080/00397911.2021.1958231 | Scopus ID | 2-s2.0-85111912219 |
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