ChemInform Abstract: A Novel Synthesis of 3,9‐Dialkyl and 8‐Aryl‐3,9‐dimethylxanthines.

Youssif, Shaker; El-Kafrawy, A.; Bayoumy, B. E.; El-Bahaie, S.

doi:10.1002/chin.200234172

Cited by 3 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1‐Methyl‐5,6‐diaminouracil was used as initial compound . Described annelation of pyrazine cycle to pyrimidine ring by [4 + 2]‐cyclocondensation of substituted 5,6‐diaminouracil with 1,2‐dicarbonyl compounds was used as synthetic approach for synthesis of target products.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives

Kazunin

Voskoboynik

Носуленко

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

in Wiley Online Library (wileyonlinelibrary.com).Synthesis of 1-methyl-6-((2-(aryl-(heteryl-))-2-oxoethyl) pteridine-2,4,7(1H,3H,8H)-triones via [4 + 2]-cycloaddition of 1-methyl-5,6-diaminouracil with ethyl 4-aryl(heteryl)-2,4-dioxobutanoates is described in presented work. It was established that the reaction occurs regioselectively and proceeds under refluxing of starting compounds in acetic acid for 60 min. The structures of synthesized compounds were proven by complex of physicochemical methods including infrared, 1 H-, 13 C-NMR spectroscopy, liquid chromatographymass spectrometry, and electron impact-mass spectrometry. Based on the detail analysis of the correlational NMR spectral data (correlation spectroscopy, heteronuclear single quantum coherence, heteronuclear multiple bond correlation, and Nuclear Overhauser effect spectroscopy), it was determined that in dimethyl sulfoxide solution, the 1-methyl-6-((2-(aryl-(heteryl-))-2-oxoethyl)pteridine-2,4,7(1H,3H,8H)-triones exist in two tautomeric forms: ketone (A) and enol (B). It was also found that tautomeric behavior of aforementioned compounds in hexadeuterated dimethyl sulfoxide is sensitive to the nature of the aryl or heteryl substituent at the position 6 of ring. The electron donating groups shift equilibrium to the tautomer A, while electron withdrawingto the tautomer B. The synthesized compounds were tested on antiradical activity. It was found that obtained compounds reveal radical scavenging activity comparable or higher than ascorbic acid.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives

Kazunin

Voskoboynik

Носуленко

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Extending our work in the synthesis of non-nucleosidic compounds of fused uracils [27,28,29], we tried to synthesize pyrimidopyridazines and pyrazolopyrimidines from 6-hydrazinyluracils. The regioselective alkylation of 6-chlorouracil 1 [30] with methyl—and/or propyl iodide in dimethyl sulfoxide (DMSO) in the presence of K 2 CO 3 as basic medium afforded about 60%–70% yield of alkylated uracils 2a – c [31,32,33,34]. The nucleophilic substitution of 6-chlorouracil 2a – c using hydrazine hydrate afforded 6-hydrazinyluracils 3a – c [34,35].…”

Section: Resultsmentioning

confidence: 99%

A Novel Synthesis of Fused Uracils: Indenopyrimidopyridazines, Pyrimidopyridazines, and Pyrazolopyrimidines for Antimicrobial and Antitumor Evalution

El‐Kalyoubi

Agili

2016

Molecules

View full text Add to dashboard Cite

Abstract:A variety of different compounds of fused uracils were prepared simply by the heating of 6-hydrazinyl-1-methyl-, 6-hydrazinyl-1-propyl-, or 6-hydrazinyl-1,3-dipropyluracil under reflux with ninhydrin, isatin, benzylidene malononitrile, benzylylidene ethyl cyanoacetate, benzil, and phenacyl bromide derivatives. The newly synthesized compounds were completely screened for antimicrobial and antitumor activity.

show abstract

“…Nowadays, uracil derivatives are successfully applied in immunotherapy and as an implement to show the stability of the properties of the cell membrane [15]. Uracil derivatives are also useful in the biosynthesis of xanthines [16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,3-Dihydro-6-methyl-2-thiopyrimidin-4(1H)-one (6-Methylthiouracil) Derivatives and Their Reactions

Barmaki

Valiyeva

Maharramovm

et al. 2013

Journal of Chemistry

View full text Add to dashboard Cite

The synthesis and characterization of 2,3-dihydro-6-methyl-2-thioxopyrimidin-(1H)-one (I) and some of its derivatives has been performed in our lab. Ring-closing cyclization, as a result of the condensation of ethyl-3-oxobutanoate with thiourea in KOH in an ethanol medium produced 2,3-dihydro-6-methy -2-thioxopyrimidin-(1H)-one (I). The reaction of compound (I) with 2- chloroacetic acid in an alkaline KOH solution produced the carboxylate derivative, 2-(2,6-dihydro-4-methyl-6-oxopyrimidin-2-yl-thio)ethanoic acid (II). The reaction of the resulted derivative of carboxylate (II) with the salt of copper sulphate, produced a new copper salt (III). A substitution reaction between synthesized compound (I) and 2-chloroethanol in an aqueous solution of KOH, created 2-(2-hydroxyethylthio)-6-methylpyrimidin-4(3H)-one (IV). The reaction of compound (I) with 2-(chloromethyl)oxirane in the presence of an aqueous solution of KOH, resulted yielded 2-(3-chloro-2-hydroxy-propylthio)-6-methylpyrimidin-4(3H)-one (V). Sodium mercaptide compound (VI), was produced by the reaction of (I) with NaOH and then the sodium salt of 2,3-dihydro-6-methyl-2-thioxopyrimidin-(1H)-one (VI) was reacted with 2-(chloromethyl)oxirane to result in 2-((oxiran-2-yl) methyl-thio)-6-methyl-pyrimidin-4(3H)-one (VII). Different acylation reagents (acetyl chloride, benzoyl chloride) were reacted with compound (I), in dimethylformamide, acylation happens on sulfur and furnished S-acylified derivatives of (VIII-IX). All the synthesized and obtained products were confirmed by IR,1H, and13C NMR and elemental analysis.

show abstract

ChemInform Abstract: A Novel Synthesis of 3,9‐Dialkyl and 8‐Aryl‐3,9‐dimethylxanthines.

Cited by 3 publications

References 1 publication

Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives

Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives

A Novel Synthesis of Fused Uracils: Indenopyrimidopyridazines, Pyrimidopyridazines, and Pyrazolopyrimidines for Antimicrobial and Antitumor Evalution

Synthesis of 2,3-Dihydro-6-methyl-2-thiopyrimidin-4(1H)-one (6-Methylthiouracil) Derivatives and Their Reactions

Contact Info

Product

Resources

About