2950-86-9Relevant articles and documents
Michael versus retro-Michael reaction in the regioselective synthesis of N-1 and N-3 uracil adducts
Boncel, S?awomir,McZka, MacIej,Walczak, Krzysztof Z.
experimental part, p. 8450 - 8457 (2010/12/25)
By controlling the temperature or reaction time in the base-catalysed Michael-type addition of 5-substituted uracil derivatives we were able to synthesise N-1 or N-3 uracil adducts using methyl acrylate and acrylonitrile as acceptors. The mechanism of this chemical inequivalence was established using 1H NMR spectroscopic studies. The investigations revealed that formation of the N-1 adduct was achievable under kinetically controlled conditions irrespective to the type of the base used (TEA, DBU). In turn, synthesis of the N-3 adducts proceeded from the initially formed N-1,N-3 diadduct via a retro-Michael reaction which dominates at elevated temperature or prolonged reaction time.
Novel acyclic amide-conjugated nucleosides and their analogues
Boncel, Slawomir,Walczak, Krzysztof
experimental part, p. 103 - 117 (2009/06/18)
An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4- methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2′- cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5′-amino- 5′-deoxythymidine and 5-aminouracil. Copyright Taylor & Francis Group, LLC.
