A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines

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.

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Synthesis of a Novel Heterocyclic System: Oxazolo[3,2-c]pyrimidine

Bakavoli

Heravi

Germaninajad

et al. 2006

Phosphorus, Sulfur, and Silicon and the Related Elements

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Keywords Heterocyclization; oxazolo pyrimidine; pyrimidine; sulfuric acid Bicyclic compounds derived from pyrimidine have critical roles in various biological processes and considerable attention has been given to the field in a search for potential antagonists. 1 It has been shown that substituted oxazolo[5,4-a]pyrimidines inhibit VEGFR 2 (vascular endotherial growth factor receptor 2, KDR) or EGFR (epidermal growth factor receptor) with/C50 values in the low nanomolar range. 2 In spite of much interest in the synthesis of oxazolopyrimidine, 1−3 a literature survey did not disclose any references concerning the synthesis of oxazolo [3,2-c]pyrimidine. In continuation of our interest concerning synthesis of nitrogen heterocycles, 4 in this article we wish to report the synthesis of oxazolo[3,2-c]pyrimidine.

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A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines

Cited by 7 publications

References 20 publications

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

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

Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives

Synthesis of a Novel Heterocyclic System: Oxazolo[3,2-c]pyrimidine

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