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  • 1
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Uracils, 5. Bridged 1,2,5,6-Tetrazocanes with Uracil and Urazole Bridges by Dimerization of 5-(1,2,4-Triazolidin-1-yl)uracilsUpon N-bromosuccinimide oxidation 5-(1,2,4-triazolidin-1-yl)uracils 3a-d, easily accessible by insertion reaction of the 4-R-TAD 1a-d to 1,3-dimethyluracil (2), react with radicalic head-to-tail dimerization to give the novel bridged 1,2,5,6-tetrazocanes 4a-d in high yield. The constitution of 4a is established by X-ray diffraction.
    Notes: Die durch Einschubreaktion der 4-R-TAD 1a-d an 1,3-Dimethyluracil (2) leicht erhältlichen 5-(1,2,4-Triazolidin-1-yl)uracile 3a-d reagieren bei N-Bromsuccinimid-Oxidation unter radikalischer Kopf-Schwanz-Dimerisierung in hohen Ausbeuten zu den neuartigen verbrückten 1,2,5,6-Tetrazocanen 4a-d. Die Konstitution von 4a wird durch Röntgenstrukturanalyse ermittelt.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 2566-2574 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Photochemistry of Heterocycles, 8. The Photoreaction of 2,5-Diaryl-1,3,4-oxadiazoles with 1,3-Dimethyluracils. A New and Simple Synthesis of 1,2,4,5-TetrazinesUpon UV-irradiation 2,5-diaryl-1,3,4-oxadiazoles 2a-g do not undergo (2 + 2)-cycloaddition with 1,3-dimethyluracil, but instead ring cleavage occurs to afford the benzoylhydrazones 3a-e as well as the decomposition products 4-6. With 6-chloro-1,3-dimethyluracil (1b) 3h is formed, which in turn photoeliminates benzoyl chloride to give the pyrazolo[3,4-d] pyrimidine 7. Saponification of 3a gives smoothly 5-benzoyl-1,3-dimethyluracil (photoselective 5-benzoylation). - A new and simple synthesis of 3,6-disubstituted 1,2,4,5-tetrazines from aroylhydrazines is described, employing the system triphenylphosphane/hexachloroethane/triethylamine.
    Notes: Die 2,5-Diaryl-1,3,4-oxadiazole 2a-g reagieren bei UV-Bestrahlung mit 1,3-Dimethyluracil nicht unter (2 + 2)-Cycloaddition sondern unter Ringspaltung von 2a-g zu den Benzoylhydrazonen 3a-e und deren Zersetzungsprodukten 4-6. Mit 6-Chlor-1,3-dimethyluracil (1b) entsteht-via Hydrazon 3h-unter Photoeliminierung von Benzoylchlorid das Pyrazolo[3,4-d]pyrimidin 7. Durch Verseifung von 3a ist 5-Benzoyl-1,3-dimethyluracil leicht zugänglich (photoselektive 5-Benzoylierung). - Eine neue und einfache Synthese von 3,6-disubstituierten 1,2,4,5-Tetrazinen aus Aroylhydrazinen und dem System Triphenylphosphan/Hexachlorethan/Triethylamin wird beschrieben.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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