21892-66-0Relevant articles and documents
Pteridines, LXXI. - Synthesis and Photochemical Behaviour of 8- Substituted Lumazines
Ram, Vishnu J.,Knappe, Wolfgang R.,Pfleiderer, Wolfgang
, p. 762 - 779 (2007/10/02)
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 photolability 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.