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

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F11%3A00361006" target="_blank" >RIV/61388963:_____/11:00361006 - isvavai.cz</a>

  • Result on the web

    <a href="http://dx.doi.org/10.1021/jo2006494" target="_blank" >http://dx.doi.org/10.1021/jo2006494</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/jo2006494" target="_blank" >10.1021/jo2006494</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

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

  • Original language description

    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 bytreatment with BBr3 gave the desired free arylated uracil bases in good yields.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

    <a href="/en/project/LC06077" target="_blank" >LC06077: Center of Chemical Genetics</a><br>

  • Continuities

    Z - Vyzkumny zamer (s odkazem do CEZ)

Others

  • Publication year

    2011

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Journal of Organic Chemistry

  • ISSN

    0022-3263

  • e-ISSN

  • Volume of the periodical

    76

  • Issue of the periodical within the volume

    13

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    11

  • Pages from-to

    5309-5319

  • UT code for WoS article

    000291920900016

  • EID of the result in the Scopus database