13964-47-1Relevant academic research and scientific papers
Photochemical reactions of 5-fluoropyrimidine bases with alcohols
Urjasz, Wojciech,Maciejewski, Andrzej,Celewicz, Lech
, p. 3243 - 3246 (2007/10/03)
Photochemical reactions of 5-fluorocytosine with primary alcohols led to 5-alkoxycytosines and 6-alkoxycytosines as the main photoproducts. These products are formed via reactive intermediates 6-alkoxy-5-fluoro-5,6- dihydrocytosines, whereas photochemical reactions of 5-fluorouracil with alcohols led to stable 6-alkoxy-5-fluoro-5,6-dihydrouracils.
Fluorinated Pyrimidines. Part 4. Synthesis, Properties and Stereochemical Conversion of the cis and trans Isomers of 6-Alkoxy-5-fluoro-5,6-dihydrouracils
Visser, Gerard W. M.,Wedzinga, Rinny,Klok, Robert P.,Herscheid, Jacobus D. M.
, p. 231 - 236 (2007/10/02)
The reaction of 6-acetoxy-5-fluoro-5,6-dihydrouracil with ROH (R=Me, Et, Pr, Pri, Bu, But) under acidic conditions has been investigated using 18F as a tracer.The quantitative replacement of the OAc-group proceeded predominantly with cisoid (gauche) stereochemistry, but upon prolonged heating the amount of the trans compound increased.This isomerization did not originate from epimerization at C5.The trans compounds-apart from being more stable towards substitution and elimination than the corresponding cis compounds-gave invariably substitution products with inversion of configuration, while the cis compounds mainly retained their configuration.Within the concept of the unifying ion-pair mechanism it is proposed that the trans compound reacts via an intimate protonated intermediate and the cis compound via a solvent-separated protonated intermediate.As a result, it was not the gauche attraction between the fluorine atom and the incoming nucleophile, but the poor ?-donor ability of the C-F bond that was the determining factor in the cisoid stereochemistry of 5-fluoro-5,6-dihydrouracil adducts.
Process for preparation of 6-substituted 5-fluorouracil derivatives
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, (2008/06/13)
The reaction of certain fluorinated pyrimidine derivatives with hydrogen donor compounds to produce 6-substituted 5-fluoropyrimidines is disclosed. The products so produced are useful in germicidal and antineoplastic applications, and can be converted into 5-fluorouracil, which has known utility in cancer chemotherapy.
