Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Abstract

1,3,5-Triazines and pyrimidine-2,4,6-triones belong to that class of compounds which are well known in literature for possessing wide range of biological activities. Here, we report a new family of compounds that encompasses these two structures. The union of both heterocycles was carried out through a hydrazone moiety incorporated into an acetyl group at the position 5 of 1,3-dimethyl pyrimidine derivative. The synthetic strategy adopted allowed the preparation of the target compounds with excellent yields and good purities. The synthesized compounds were well characterized by NMR (1H and 13C), HRMS, and elemental analysis. Furthermore, the tautomerism of enhydrazine versus hydrazone has also been studied.

Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity

“…Satisfactory yields of compounds A08 and A09 were obtained, respectively (Scheme ). The spectral data confirmed their enamine structures rather than imine structures, which were in good agreement with the reported data …”

“…Acylation : Although BA acetylation can be achieved by several methods, there is no appropriate or concrete evidence of TBA acetylation. Using DETBA as the substrate, acylation of TBA with acetic/propionic anhydride was performed following our previously reported method for BA with slight modifications (Scheme ). The use of aqueous media for this reaction and a small excess of anhydride is an advantage over the previously reported method .…”

Synthesis and Characterization of Some 5-Acetylbarbituric Based Thiosemicarbazone Derivatives

“…The 1 H NMR spectra of these synthesized compounds, showed two characteristic signals in the range of δ 2.5 to 2.6 ppm and 13.0 to 13.6 ppm due to C-CH3 and N2H protons, respectively. The 1 H NMR spectra of Acb4NDH and the N-monosubstituted thiosemicarbazones (1)(2)(3) show a signal in the range of 9.9-10.1 ppm due to the N3H proton, while in the spectra of the N-disubstituted thiosemicarbazones (4)(5)(6), this signal is absent, appearing a new signal at 2.45 ppm attributed to the proton C6H (Figure 1). This fact reflects the keto/exo-enol tautomerism present in solution (Scheme 2).…”

“…On the other hand, the medical importance of many pyrimidine derivatives is significant since they have antineoplastic, antiviral, antibiotic and anti-inflammatory properties, among other biological activities. Many synthetic molecules containing pyrimidine, such as certain barbituric acid derivatives or the sulfadiazine, are also important as synthetic drugs and chemotherapeutic agents, and have been developed using the small 5-acylbarbiturate moieties as the main building block in their preparation [5].…”

s-Triazine: A Privileged Structure for Drug Discovery and Bioconjugation

“…Filtration and drying afforded the desired products (14 derivatives) [21]. Hydrazone derivatives bearing a s-triazine core (Series 3 and 4) were synthesized [13,15,24]. Disubstituted-monochloro triazines (d-MCTs) were synthesized using piperidine and morpholine as nucleophiles.…”