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- W2040753609 abstract "Ausgehend von 6-Chlor-5-nitrouracil (1) und seinem 3-Methyl-Derivat 2 warden über die entsprechenden am Aminostickstoff substituierten 6-Amino-5-nitrouracile 3–26 die 8-substituierten Lumazine 34–69 dargestellt. Ihr photochemisches Verhalten wird untersucht. In Abhängigkeit von der chemischen Natur der N-8-Seitenkette laufen unterschiedliche Photoreaktionen ab von denen vor allem die leichte Photodealkylierung der β-Hydroxy-, β-Methoxy- und β-Aminoethyl-Derivate 34–44 herausragt. Mit zunehmender Donatoreigenschaft des β-Substituenten steigt auch die Photolabilität, die sich in einer Norrish-Typ-II-Spaltung zu den entsprechenden Lumazinen 70–75 kundtut. Die 8-Cycloalkyllumazine 52–54 erleiden eine Photoreduktion zu den 7,8-Dihydrolumazinen 76–78. Sämtliche neuen 8-substituierten Lumazine werden durch Analysen und UV-Spektren charakterisiert und strukturelle Besonderheiten, bedingt durch die verschiedenen Substituenten in 6-, 7- und 8-Stellung, diskutiert. Pteridines, LXXI1). — Synthesis and Photochemical Behaviour of 8-Substituted Lumazines The 8-substituted lumazines 34–69 have been synthesized from 6-chloro-5-nitrouracil (1) and its 3-methyl derivative 2 via the corresponding 6-amino-5-nitrouracils 3–26, substituted at the amino nitrogen. The photochemical properties of the 8-substituted lumazines have been investigated. Various photoreactions were observed depending on the chemical nature of the N-8 side-chain and leading to an easy photodealkylation of the β-hydroxy-, β-methoxy-, and β-aminoethyl derivatives 34–44. Increasing donor properties of the β-substituent enhances the photolabilty which is expressed in a Norrish-type II cleavage reaction to the corresponding lumazines 70–75. 8-Cycloalkyllumazines 52–54 show photoreduction to 7,8-dihydrolumazines 76–78. The newly synthesized 8-substituted lumazine derivatives have been characterized by elementary analyses and UV spectra. Structural peculiarities due to the various substituents in position 6, 7, and 8 will be discussed." @default.
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- W2040753609 date "1982-04-20" @default.
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- W2040753609 title "Pteridine, LXXI. Synthese und photochemisches Verhalten von 8-substituierten Lumazinen" @default.
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- W2040753609 doi "https://doi.org/10.1002/jlac.198219820418" @default.
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