Počet záznamů: 1

Regioselective Direct C-H Arylations of Protected Uracils. Synthesis of 5- and 6-Aryluracil Bases

  1. 1.
    0361006 - UOCHB-X 2012 RIV US eng J - Článek v odborném periodiku
    Čerňová, Miroslava - Čerňa, Igor - Pohl, Radek - Hocek, Michal
    Regioselective Direct C-H Arylations of Protected Uracils. Synthesis of 5- and 6-Aryluracil Bases.
    Journal of Organic Chemistry. Roč. 76, č. 13 (2011), s. 5309-5319 ISSN 0022-3263
    Grant CEP: GA MŠk(CZ) LC06077
    Výzkumný záměr: CEZ:AV0Z40550506
    Klíčová slova: pyrimidines * uracil * direct C-H arylations * palladium
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 4.450, rok: 2011

    A new regioselective synthesis of 5- and 6-aryluracil bases has been developed based on direct C-H arylations of diverse 1,3-protected uracils. Benzyl-protected uracils were selected as the most practical in terms of stability during the arylation and facile cleavage of the benzyl groups. Pd-catalyzed C-H arylations in absence of CuI gave preferentially 5-aryl-, whereas the reactions in presence of CuI gave 6-aryl-1,3-dibenzyluracils. Final deprotection either by transfer hydrogenolysis over Pd/C or by treatment with BBr3 gave the desired free arylated uracil bases in good yields.
    Trvalý link: http://hdl.handle.net/11104/0198426